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Journal articles on the topic 'Carboxyl and acyl transfer reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Bérces, Attila, Dennis M. Whitfield, Tomoo Nukada, Iwona do Santos Z., Agnes Obuchowska, and Jiri J. Krepinsky. "Is acyl migration to the aglycon avoidable in 2-acyl assisted glycosylation reactions?" Canadian Journal of Chemistry 82, no. 7 (2004): 1157–71. http://dx.doi.org/10.1139/v04-059.

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This report unequivocally separates orthoester formation from acyl transfer for the first time and indicates possible routes to eliminate 2-O-acyl transfer during glycosylation reactions. Experimental evidence is shown that acyl transfer from 2-O-acyl-3,4,6-tri-O-benzyl-D-galactopyranose-derived glycosyl donors decreases in the order formyl > acetyl > pivaloyl. The 2-O-benzoyl derivatives are more variable, in some cases transferring easily, and in others not at all. Density functional theory (DFT) calculations of the structure and energetics of dioxolenium ion and related intermediates suggest that a proton transfer pathway from the nucleophile to O-2 provides an explanation for the observed trends. These DFT calculations of the proton transfer pathway support a mechanism in which a relay molecule is involved. Further DFT calculations used a constraint based on linear combinations of six bond lengths to establish the sequence of bond breaking and bond forming. The calculated anomeric carbon to former carbonyl oxygen bond that breaks during acyl transfer is the longest in the formyl case and shortest in those that exhibit little or no acyl transfer. Rotation about the aromatic to carbonyl PhC(=O) bond is different from the alkyl series. Analysis of this proposed TS led to the postulate that 2,6-substitution may hinder rotation even more. Thus, the 2,6-dimethylbenzoyl analogue was synthesized and it does not transfer directly or by rearrangement of its readily formed orthoester. DFT calculations suggested that 2,6-dimethoxybenzoyl should also not transfer easily. Experimentally, this proved to be the case and this new 2-O-acyl protecting group cleaves at 50 °C with a 1 mol/L solution of LiOH in methanol. Thus, a calculated transition state has led to a prototype of a protecting group that solves a major problem in oligosaccharide synthesis.Key words: glycosylation, carbohydrates, quantum chemistry, reaction mechanism, neighboring-group effects.

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2

Nguyen-Distèche, M., M. Leyh-Bouille, S. Pirlot, J. M. Frère, and J. M. Ghuysen. "Streptomyces K15 dd-peptidase-catalysed reactions with ester and amide carbonyl donors." Biochemical Journal 235, no. 1 (1986): 167–76. http://dx.doi.org/10.1042/bj2350167.

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In water, the purified 26 000-Mr membrane-bound DD-peptidase of Streptomyces K15 hydrolyses the ester carbonyl donor Ac2-L-Lys-D-Ala-D-lactate (release of D-lactate) and the amide carbonyl donor Ac2-L-Lys-D-Ala-D-Ala (release of D-alanine) with accumulation of acyl- (Ac2-L-Lys-D-alanyl-)enzyme. Whereas hydrolysis of the ester substrate proceeds to completion, hydrolysis of the amide substrate is negligible because of the capacity of the K15 DD-peptidase for utilizing the released D-alanine in a transfer reaction (Ac2-L-Lys-D-Ala-D-Ala + D-Ala→Ac2-L-Lys-D-Ala-D-Ala + D-Ala) that maintains the concentration of the amide substrate at a constant level. In the presence of an amino acceptor X-NH2 (Gly-Gly or Gly-L-Ala) related to the Streptomyces peptidoglycan, both amide and ester carbonyl donors are processed without detectable accumulation of acyl-enzyme. Under proper conditions, the acceptor activity of water and, in the case of the amide substrate, the acceptor activity of the released D-alanine can be totally overcome so that the two substrates are quantitatively converted into transpeptidated product Ac2-L-Lys-D-Ala-NH-X (and hydrolysis is prevented). Experimental evidence suggests that the amino acceptor modifies both the binding of the carbonyl donor to the enzyme and the ensuing rate of enzyme acylation.

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3

Portada, Tomislav, Davor Margetić, and Vjekoslav Štrukil. "Mechanochemical Catalytic Transfer Hydrogenation of Aromatic Nitro Derivatives." Molecules 23, no. 12 (2018): 3163. http://dx.doi.org/10.3390/molecules23123163.

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Mechanochemical ball milling catalytic transfer hydrogenation (CTH) of aromatic nitro compounds using readily available and cheap ammonium formate as the hydrogen source is demonstrated as a simple, facile and clean approach for the synthesis of substituted anilines and selected pharmaceutically relevant compounds. The scope of mechanochemical CTH is broad, as the reduction conditions tolerate various functionalities, for example nitro, amino, hydroxy, carbonyl, amide, urea, amino acid and heterocyclic. The presented methodology was also successfully integrated with other types of chemical reactions previously carried out mechanochemically, such as amide bond formation by coupling amines with acyl chlorides or anhydrides and click-type coupling reactions between amines and iso(thio)cyanates. In this way, we showed that active pharmaceutical ingredients Procainamide and Paracetamol could be synthesized from the respective nitro-precursors on milligram and gram scale in excellent isolated yields.

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4

Yang, Haoyang, Biao Zhang, Wentao Zhong, Zhisheng Fu, and Zhiqiang Fan. "Modification of the Acyl Chloride Quench-Labeling Method for Counting Active Sites in Catalytic Olefin Polymerization." Catalysts 11, no. 6 (2021): 683. http://dx.doi.org/10.3390/catal11060683.

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The reliable and efficient counting of active sites in catalytic olefin polymerization has been realized by using acyl chloride as the quench-labeling agent. However, the molar ratio of acyl chloride to the alkylaluminum cocatalyst must be larger than 1 in order to completely depress side reactions between the quencher and Al-polymeryl that is formed via chain transfer reaction. In this work, a tetrahydrofuran/thiophene-2-carbonyl chloride (THF/TPCC) mixture was used as the quenching agent when counting the active sites of propylene polymerization catalyzed by MgCl2/Di/TiCl4 (Di = internal electron donor)-type Ziegler–Natta catalyst activated with triethylaluminum (TEA). When the THF/TEA molar ratio was 1 and the TPCC/TEA molar ratio was smaller than 1, the [S]/[Ti] ratio of the polymer quenched with the THF/TPCC mixture was the same as that quenched with only TPCC at TPCC/TEA > 1, indicating quench-labeling of all active sites bearing a propagation chain. The replacement of a part of the TPCC with THF did not influence the precision of active site counting by the acyl chloride quench-labeling method, but it effectively reduced the amount of acyl chloride. This modification to the acyl chloride quench-labeling method significantly reduced the amount of precious acyl chloride quencher and brought the benefit of simplifying polymer purification procedures after the quenching step.

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5

Grandchamps, J., M. Nguyen-Distèche, C. Damblon, J. M. Frère, and J. M. Ghuysen. "Streptomyces K15 active-site serine dd-transpeptidase: specificity profile for peptide, thiol ester and ester carbonyl donors and pathways of the transfer reactions." Biochemical Journal 307, no. 2 (1995): 335–39. http://dx.doi.org/10.1042/bj3070335.

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The Streptomyces K15 transferase is a penicillin-binding protein presumed to be involved in bacterial wall peptidoglycan crosslinking. It catalyses cleavage of the peptide, thiol ester or ester bond of carbonyl donors Z-R1-CONH-CHR2-COX-CHR3-COO- (where X is NH, S or O) and transfers the electrophilic group Z-R1-CONH-CHR2-CO to amino acceptors via an acyl-enzyme intermediate. Kinetic data suggest that the amino acceptor behaves as a simple alternative nucleophile at the level of the acyl-enzyme in the case of thiol ester and ester donors, and that it binds to the enzyme.carbonyl donor Michaelis complex and influences the rate of enzyme acylation by the carbonyl donor in the case of amide donors. Depending on the nature of the scissile bond, the enzyme has different requirements for substituents at positions R1, R2 and R3.

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6

Dasgupta, Sayani, Sharmishtha Samantaray, Dinkar Sahal, and Rajendra P. Roy. "Isopeptide Ligation Catalyzed by Quintessential Sortase A." Journal of Biological Chemistry 286, no. 27 (2011): 23996–4006. http://dx.doi.org/10.1074/jbc.m111.247650.

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The housekeeping transpeptidase sortase A (SrtA) from Staphyloccocus aureus catalyzes the covalent anchoring of surface proteins to the cell wall by linking the threonyl carboxylate of the LPXTG recognition motif to the amino group of the pentaglycine cross-bridge of the peptidoglycan. SrtA-catalyzed ligation of an LPXTG containing polypeptide with an aminoglycine-terminated moiety occurs efficiently in vitro and has inspired the use of this enzyme as a synthetic tool in biological chemistry. Here we demonstrate the propensity of SrtA to catalyze “isopeptide” ligation. Using model peptide sequences, we show that SrtA can transfer LPXTG peptide substrates to the ϵ-amine of specific Lys residues and form cyclized and/or a gamut of branched oligomers. Our results provide insights about principles governing isopeptide ligation reactions catalyzed by SrtA and suggest that although cyclization is guided by distance relationship between Lys (ϵ-amine) and Thr (α-carboxyl) residues, facile branched oligomerization requires the presence of a stable and long-lived acyl-enzyme intermediate.

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7

Viswambharan, Baby, Tatsuya Okimura, Satoko Suzuki, and Sentaro Okamoto. "Synthesis and Catalytic Properties of 4-Aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles for Asymmetric Acyl or Carboxyl Group Transfer Reactions." Journal of Organic Chemistry 76, no. 16 (2011): 6678–85. http://dx.doi.org/10.1021/jo200984n.

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8

Buckel, Wolfgang, Berta M. Martins, Albrecht Messerschmidt, and Bernard T. Golding. "Radical-mediated dehydration reactions in anaerobic bacteria." Biological Chemistry 386, no. 10 (2005): 951–59. http://dx.doi.org/10.1515/bc.2005.111.

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AbstractMost dehydratases catalyse the elimination of water from β-hydroxy ketones, β-hydroxy carboxylic acids or β-hydroxyacyl-CoA. The electron-withdrawing carbonyl functionalities acidify the α-hydrogens to enable their removal by basic amino acid side chains. Anaerobic bacteria, however, ferment amino acids via α- or γ-hydroxyacyl-CoA, dehydrations of which involve the abstraction of a β-hydrogen, which is ostensibly non-acidic (pKca. 40). Evidence is accumulating that β-hydrogens are acidified via transient conversion of the CoA derivatives to enoxy radicals by one-electron transfers, which decrease the pKto 14. The dehydrations of (R)-2-hydroxyacyl-CoA to (E)-2-enoyl-CoA are catalysed by heterodimeric [4Fe-4S]-containing dehydratases, which require reductive activation by an ATP-dependent one-electron transfer mediated by a homodimeric protein with a [4Fe-4S] cluster between the two subunits. The electron is further transferred to the substrate, yielding a ketyl radical anion, which expels the hydroxyl group and forms an enoxy radical. The dehydration of 4-hydroxybutyryl-CoA to crotonyl-CoA involves a similar mechanism, in which the ketyl radical anion is generated by one-electron oxidation. The structure of the FAD- and [4Fe-4S]-containing homotetrameric dehydratase is related to that of acyl-CoA dehydrogenases, suggesting a radical-based mechanism for both flavoproteins.

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9

Ghuysen, J. M., J. M. Frère, M. Leyh-Bouille, M. Nguyen-Distèche, and J. Coyette. "Active-site-serine d-alanyl-d-alanine-cleaving-peptidase-catalysed acyl-transfer reactions. Procedures for studying the penicillin-binding proteins of bacterial plasma membranes." Biochemical Journal 235, no. 1 (1986): 159–65. http://dx.doi.org/10.1042/bj2350159.

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Under certain conditions, the values of the parameters that govern the interactions between the active-site-serine D-alanyl-D-alanine-cleaving peptidases and both carbonyl-donor substrates and beta-lactam suicide substrates can be determined on the basis of the amounts of (serine ester-linked) acyl-protein formed during the reactions. Expressing the ‘affinity’ of a beta-lactam compound for a DD-peptidase in terms of second-order rate constant of enzyme acylation and first-order rate constant of acyl-enzyme breakdown rests upon specific features of the interaction (at a given temperature) and permits study of structure-activity relationships, analysis of the mechanism of intrinsic resistance and use of a ‘specificity index’ to define the capacity of a beta-lactam compound of discriminating between various sensitive enzymes. From knowledge of the first-order rate constant of acyl-enzyme breakdown and the given time of incubation, the beta-lactam compound concentrations that are necessary to achieve given extents of DD-peptidase inactivation can be converted into the second-order rate constant of enzyme acylation. The principles thus developed can be applied to the study of the multiple penicillin-binding proteins that occur in the plasma membranes of bacteria.

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10

Viswambharan, Baby, Tatsuya Okimura, Satoko Suzuki, and Sentaro Okamoto. "ChemInform Abstract: Synthesis and Catalytic Properties of 4-Aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles for Asymmetric Acyl or Carboxyl Group Transfer Reactions." ChemInform 42, no. 50 (2011): no. http://dx.doi.org/10.1002/chin.201150146.

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11

Wolfe, Saul, Haolun Jin, Kiyull Yang, Chan-Kyung Kim, and Ernest McEachern. "Interactive design and synthesis of a novel antibacterial agent." Canadian Journal of Chemistry 72, no. 4 (1994): 1051–65. http://dx.doi.org/10.1139/v94-133.

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β-Lactam compounds act on penicillin-recognizing enzymes via acylation of the hydroxyl group of an active site serine. When the resulting acyl enzyme is kinetically stable, as in the case of a penicillin-binding protein (PBP), the biosynthesis of a bacterial cell wall is inhibited, and death of the organism results. The de novo design of an antibacterial agent targeted to a PBP might be possible if the three-dimensional structural requirements of the equilibrium (i.e, fit) and catalytic (i.e. reactivity) steps of the aforementioned enzymatic process could be determined. For a model of the active site of a PBP from Streptomyces R61, the use of molecular mechanics calculations to treat "fit," and ab initio molecular orbital calculations to treat "reactivity," leads to the idea that the carboxyl group (G1) and the amide N-H (G2) of the antibiotic are hydrogen bonded to a lysine amino group and a valine carbonyl group in the enzyme–substrate complex. These two hydrogen bonds place the serine hydroxyl group on the convex face of the antibiotic, in position for attack on the β-lactam ring by a neutral reaction, catalyzed by water, that involves a direct proton transfer to the β-lactam nitrogen. Molecular orbital calculations of structure–reactivity relations associated with this mechanism suggest that C=N is bioisosteric to the β-lactam N-C(=O), comparable to a β-lactam in its reactivity with an alcohol, and that the product RO(C-N)H is formed essentially irreversibly (−ΔE > 10 kcal/mol). Accordingly, structures containing a G1 and a G2 separated by a C=N, and positioned in different ways with respect to this functional group, have been synthesized computationally and examined for their ability to fit to the PBP model. This strategy identified a 2H-5,6-dihydro-1,4-thiazine substituted by hydroxyl and carboxyl groups as a target for chemical synthesis. However, exploratory experiments suggested that the C=N of this compound equilibrates with endocyclic and exocyclic enamine tautomers. This required that the C2 position be substituted, and that the hydroxyl group not be attached to the carbon atom adjacent to the C=N. These conditions are met in a 2,2-dimethyl-3-(2-hydroxypropyl)-1,4-thiazine, which also exhibits the necessary fit to the PBP model. Two epimers of this compound have been synthesized, from D- and L-serine. The compound derived from L-serine is not active. The compound derived from D-serine exhibits antibacterial activity, but is unstable, and binding studies with PBP's have not been performed. It is hoped that these studies can be carried out if modification of the lead structure leads to compounds with improved chemical stability.

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12

Liepa, AJ, AJ Liepa, TC Morton та TC Morton. "Synthesis of 1-(α-Acyloxy-2-hydroxybenzyl)Azoles and Related Compounds by an Acyl Transfer Reaction". Australian Journal of Chemistry 42, № 11 (1989): 1961. http://dx.doi.org/10.1071/ch9891961.

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Novel azole adducts were produced by reaction of azoles and 2-acyloxyaryl aldehydes. The mechanism of the reaction involves attack by the azole at the carbonyl group and transfer of the acyl group to form an azole-substituted benzylic ester. 2-Acyloxyaryl ketones did not undergo an analogous reaction. An aminal was formed rather than an azole-substituted benzylic carbonate when a 2-aryl aldehyde carbonate was used as substrate.

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13

Symes, Jill, and Tomasz A. Modro. "Phosphoryl to carbonyl migration of amino groups in mixed anhydrides." Canadian Journal of Chemistry 64, no. 9 (1986): 1702–8. http://dx.doi.org/10.1139/v86-280.

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Mixed anhydrides derived from carboxylic and amidophosphoric acids, (RO)(R′2N)P(O)OC(O)R″ (1), undergo unimolecular fragmentation yielding carboxyamides, R″C(O)NR′2, and metaphosphate esters, ROPO2. The mechanism of the amino group transfer was studied for substrate 1a (1, R = R′ = Me; R″ = Ph); solvent as well as substituent effects indicate little (if any) charge development in the transition state. The effects of solvents and Lewis acids on the reaction rate and the activation parameters determined for 1a can be explained best in terms of stabilizing interactions with either carboxyamide or metaphosphate being formed in the course of reaction. The transfer of a functional group from one acyl center to another was investigated for other anhydride systems and the relative contributions of the fragmentation vs. disproportionation of substrates are discussed.

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14

Guthrie, J. Peter, and David C. Pike. "Hydration of acylimidazoles: tetrahedral intermediates in acylimidazole hydrolysis and nucleophilic attack by imidazole on esters. The question of concerted mechanisms for acyl transfers." Canadian Journal of Chemistry 65, no. 8 (1987): 1951–69. http://dx.doi.org/10.1139/v87-326.

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Heats of hydrolysis have been measured for three acylimidazole acetals. From these results free energies of formation in aqueous solution have been calculated for the acetals and the corresponding tetrahedral intermediates. Having free energies of formation for the tetrahedral intermediates allows a detailed analysis of the energetics of both the unobservable nucleophilic reaction of imidazole with ethyl acetate and also the observable reaction of imidazole with p-nitrophenyl acetate. pKa values of 1-(3-aminopropyl)-imidazole and 1-(2-aminoethyl)-imidazole have been determined to allow calculation of the σ* value for the imidazolyl substituent. The dependence of imidazole pKa values on the electron-withdrawing properties of the 1-substituent was also determined. There is a linear free energy relation between the free energy change for replacement of OH in a carbonyl hydrate by imidazolyl and the sum of the σ* values for the other substituents. The implications of these results for the question of concerted versus stepwise mechanisms for the reactions of imidazole with aryl acetates have been examined. An equilibrium constant has been calculated for the addition of imidazole to p-nitrophenyl acetate. A simple extension of Marcus theory allows the free energy surface for a three-dimensional reaction coordinate diagram to be calculated using the energy levels of the tetrahedral intermediate determined in this work, the energy level of the acylium ion derived from literature data, and intrinsic barriers for the edge reactions. It is shown that the reaction of imidazole with p-nitrophenyl acetate probably follows a concerted path. General conclusions from this theory of concerted reactions are discussed.

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15

Shashidhar, Mysore S., and Shobhana Krishnaswamy. "Intermolecular Acyl-Transfer Reactions in Molecular Crystals." Accounts of Chemical Research 52, no. 2 (2019): 437–46. http://dx.doi.org/10.1021/acs.accounts.8b00557.

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16

Hillenbrand, Eric A., and Steve Scheiner. "Analysis of the principles governing proton-transfer reactions. Carboxyl group." Journal of the American Chemical Society 108, no. 23 (1986): 7178–86. http://dx.doi.org/10.1021/ja00283a007.

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17

Williams, Andrew. "Concerted mechanisms of acyl group transfer reactions in solution." Accounts of Chemical Research 22, no. 11 (1989): 387–92. http://dx.doi.org/10.1021/ar00167a003.

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18

Arisawa, Mieko, Yui Igarashi, Haruki Kobayashi, et al. "Equilibrium shift in the rhodium-catalyzed acyl transfer reactions." Tetrahedron 67, no. 40 (2011): 7846–59. http://dx.doi.org/10.1016/j.tet.2011.07.031.

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19

Simanenko, Yu S., A. F. Popov, T. M. Prokop'eva, V. A. Savelova, and I. A. Belousova. "Hydroxylamine anion ? an effective ?-nucleophile in acyl transfer reactions." Theoretical and Experimental Chemistry 30, no. 2 (1994): 61–64. http://dx.doi.org/10.1007/bf00530586.

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20

Sun, Yue-Wei, and Lan-Zhi Wang. "One-pot synthesis of novel functionalized benzodiazepines via three-component or domino reactions." New Journal of Chemistry 42, no. 24 (2018): 20032–40. http://dx.doi.org/10.1039/c8nj04893b.

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A simple and highly efficient protocol for the one-pot synthesis of novel benzodiazepines, which fused tricyclic or tetracyclic systems containing aryl, carboxyl, ester and acyl groups, was developed. Libraries of 40 new compounds were successfully synthesized via three-component or domino reactions by using a mild catalyst (γ-Fe<sub>2</sub>O<sub>3</sub>@SiO<sub>2</sub>/CeCl<sub>3</sub>) in good to excellent yields (82–97%).

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21

Couture, Philippe, and John Warkentin. "Chemistry of cyclic aminooxycarbenes." Canadian Journal of Chemistry 75, no. 9 (1997): 1281–94. http://dx.doi.org/10.1139/v97-154.

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A series of oxazolidin-2-ylidenes and one tetrahydro-1,3-oxazin-2-ylidene, generated by thermolysis of Δ3-1,3,4-oxadiazolines in benzene at 90 °C, were intercepted by insertion into the OH bond of phenols. In two cases the initial products rearranged to N-(2-aryloxyethyl)-N-methylformamides. The activation energy for rotation about the amide CN bond of those ultimate products was measured as 20.4 kcal/mol. The aminooxycarbenes reacted with two equivalents of methyl or phenyl isocyanate to give spiro-fused hydantoins. Major products from the reactions of the N-carbonyl carbenes with dimethyl acetylenedicarboxylate or with methyl propiolate were 2-oxazolines resulting from apparent acyl transfers from N to C in the proposed dipolar intermediates; minor products of 1:2 (carbene:trap) stoichiometry were also observed. Keywords: nucleophilic carbene, aminooxycarbene, oxadiazoline, amide rotation, oxazolidine.

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22

Lobo, Ana M., M. Matilde Marques, Sundaresan Prabhakar, and Henry S. Rzepa. "Tetrahedral intermediates formed during acyl transfer. Reactions of acetyl cyanide." Journal of the Chemical Society, Chemical Communications, no. 16 (1985): 1113. http://dx.doi.org/10.1039/c39850001113.

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23

van Axel Castelli, Valeria, Roberta Cacciapaglia, Gabriela Chiosis, Frank C. J. M. van Veggel, Luigi Mandolini, and David N. Reinhoudt. "The uranyl unit as electrophilic catalyst of acyl transfer reactions." Inorganica Chimica Acta 246, no. 1-2 (1996): 181–93. http://dx.doi.org/10.1016/0020-1693(96)05065-7.

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24

Prokop?eva, T. M., Yu S. Simanenko, E. A. Karpichev, V. A. Savelova, and A. F. Popov. "O-nucleophilic features of amidoximes in acyl group transfer reactions." Russian Journal of Organic Chemistry 40, no. 11 (2004): 1617–29. http://dx.doi.org/10.1007/s11178-005-0068-3.

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25

Smith, A. D., and P. A. Woods. "ChemInform Abstract: Non-DMAP-Type Catalysts for Acyl Transfer Reactions." ChemInform 44, no. 8 (2013): no. http://dx.doi.org/10.1002/chin.201308203.

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26

Furuta, T., and T. Kawabata. "ChemInform Abstract: Chiral DMAP-Type Catalysts for Acyl Transfer Reactions." ChemInform 44, no. 8 (2013): no. http://dx.doi.org/10.1002/chin.201308204.

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27

Attwood, Paul V., and John C. Wallace. "Chemical and Catalytic Mechanisms of Carboxyl Transfer Reactions in Biotin-Dependent Enzymes." Accounts of Chemical Research 35, no. 2 (2002): 113–20. http://dx.doi.org/10.1021/ar000049+.

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28

Gravel, Christian, Danielle Lapierre, Judith Labelle, and Jeffrey W. Keillor. "Acyl transfer from carboxylate, carbonate, and thiocarbonate esters to enzymatic and nonenzymatic thiolates." Canadian Journal of Chemistry 85, no. 3 (2007): 164–74. http://dx.doi.org/10.1139/v07-011.

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Transglutaminases (EC 2.3.2.13) (TGases) catalyze calcium-dependent acyl transfer reactions between peptide-bound glutamine residues as acyl donors and peptide-bound lysine residues as acyl acceptors, resulting in the formation of intermolecular ε-(γ-glutamyl)lysine crosslinks. The mechanistic details of its "ping-pong" transamidation reaction remain unknown. In particular, few studies have been published probing the nucleophilicity of TGase using acyl-donor substrates of varied electrophilicity. Herein we report the synthesis of activated esters of carbonates, carbamates, and thiocarbonates and their reactions with simple thiols, as a nonenzymatic point of reference, and with the catalytic cysteine residue of guinea pig liver TGase. Our kinetic results show that the simple substitution of a side chain methylene unit by oxygen or sulphur had a surprising effect on both substrate affinity and acylation reactivity. Furthermore, they provide unexpected insight into the importance of a side chain heteroatom for conferring affinity for tissue TGase as well as revealing an interesting class of irreversible inhibitors.Key words: enzyme kinetics, enzyme inhibition, transglutaminase, acyl-transfer reactions, carbamate, thiocarbonate, carbonate.

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29

Lee, Ikchoon, and Dae Sung. "Theoretical and Physical Aspects of Stepwise Mechanisms in Acyl-Transfer Reactions." Current Organic Chemistry 8, no. 7 (2004): 557–67. http://dx.doi.org/10.2174/1385272043370753.

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30

McGrath, Nicholas A., and Ronald T. Raines. "Chemoselectivity in Chemical Biology: Acyl Transfer Reactions with Sulfur and Selenium." Accounts of Chemical Research 44, no. 9 (2011): 752–61. http://dx.doi.org/10.1021/ar200081s.

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31

Boulton, Lee T., Martin E. Fox, Paul B. Hodgson, and Ian C. Lennon. "Zinc-mediated intramolecular acyl and imino transfer reactions of aryl iodides." Tetrahedron Letters 46, no. 6 (2005): 983–86. http://dx.doi.org/10.1016/j.tetlet.2004.12.034.

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32

Spivey, Alan C., and Stellios Arseniyadis. "ChemInform Abstract: Amine, Alcohol and Phosphine Catalysts for Acyl Transfer Reactions." ChemInform 42, no. 23 (2011): no. http://dx.doi.org/10.1002/chin.201123229.

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33

Sträter, Norbert, William N. Lipscomb, Thomas Klabunde, and Bernt Krebs. "Two-Metal Ion Catalysis in Enzymatic Acyl- and Phosphoryl-Transfer Reactions." Angewandte Chemie International Edition in English 35, no. 18 (1996): 2024–55. http://dx.doi.org/10.1002/anie.199620241.

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34

Hamuro, Yoshitomo, Mark A. Scialdone, and William F. DeGrado. "Resin-to-Resin Acyl- and Aminoacyl-Transfer Reactions Using Oxime Supports." Journal of the American Chemical Society 121, no. 8 (1999): 1636–44. http://dx.doi.org/10.1021/ja9818654.

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35

Gonnade, Rajesh G., and Mysore S. Shashidhar. "Acyl-transfer reactions in molecular crystals: reactivity correlation with crystal structure." Acta Crystallographica Section A Foundations and Advances 73, a2 (2017): C771. http://dx.doi.org/10.1107/s2053273317088039.

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36

Müller, Christian E., Daniela Zell, Radim Hrdina, et al. "Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols." Journal of Organic Chemistry 78, no. 17 (2013): 8465–84. http://dx.doi.org/10.1021/jo401195c.

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37

Jönsson, Åsa, Ernst Wehtje, Patrick Adlerreutz, and Bo Mattiasson. "Temperature effects on protease catalyzed acyl transfer reactions in organic media." Journal of Molecular Catalysis B: Enzymatic 2, no. 1 (1996): 43–51. http://dx.doi.org/10.1016/1381-1177(96)00010-0.

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38

Lawrence, James B., Patrick Moreau, Claude Cassagne, and D. James Morré. "Acyl transfer reactions associated with cis Golgi apparatus of rat liver." Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1210, no. 2 (1994): 146–50. http://dx.doi.org/10.1016/0005-2760(94)90114-7.

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39

Schellenberger, Volker, Ute Schellenberger, Yuri V. Mitin, and Hans-Dieter Jakubke. "An apparatus for continuous analysis of protease-catalyzed acyl transfer reactions." Analytical Biochemistry 165, no. 2 (1987): 327–30. http://dx.doi.org/10.1016/0003-2697(87)90276-4.

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40

Erben, Anne, Tom N. Grossmann, and Oliver Seitz. "DNA-instructed acyl transfer reactions for the synthesis of bioactive peptides." Bioorganic & Medicinal Chemistry Letters 21, no. 17 (2011): 4993–97. http://dx.doi.org/10.1016/j.bmcl.2011.05.027.

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41

Sophiamma, P. N., and K. Sreekumar. "Effect of polymer architecture on the efficiency of acyl transfer reactions." Journal of Applied Polymer Science 62, no. 10 (1996): 1753–59. http://dx.doi.org/10.1002/(sici)1097-4628(19961205)62:10<1753::aid-app29>3.0.co;2-0.

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42

Öhrner, Niklas, Mats Martinelle, Anders Mattson, Torbjörn Norin, and Karl Hult. "Thioethyl-, Vinyl-, Ethyl Octanoate Esters and Octanoic Acid as Acyl Donors in Lipase Catalysed Acyl Transfer Reactions." Biocatalysis 9, no. 1-4 (1994): 105–14. http://dx.doi.org/10.3109/10242429408992112.

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43

Gololobov, M. Y., та R. C. Bateman. "γ-Glutamyltranspeptidase-catalysed acyl-transfer to the added acceptor does not proceed via the ping-pong mechanism". Biochemical Journal 304, № 3 (1994): 869–76. http://dx.doi.org/10.1042/bj3040869.

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Abstract:

Acyl-transfer catalysed by gamma-glutamyltranspeptidase from bovine kidney was studied using gamma-L- and gamma-D-Glu-p-nitroanilide as the donor and GlyGly as the acceptor. The transfer of the gamma-Glu group to GlyGly was shown to be accompanied by transfer of the gamma-Glu group to water (hydrolysis). The results were compared with acyl-transfer catalysed by the representative serine protease, alpha-chymotrypsin. The main difference between the kinetic mechanism of the acyl-transfer reactions catalysed by these enzymes, which contain an active-site serine and form an acyl-enzyme intermediate but belong to different enzyme classes, was found to consist in the role of the enzyme-donor-acceptor complex. This complex is not formed at any acceptor concentrations in the acyl-transfer reactions catalysed by the serine proteases. In contrast, in the gamma-glutamyltranspeptidase-catalysed acyl-transfer the pathway going through the ternary enzyme-donor-acceptor complex formed from the enzyme-acceptor complex becomes the main pathway of the transfer reaction even at moderate acceptor concentrations. As a result, gamma-glutamyltranspeptidase catalysis follows a sequential mechanism with random equilibrium addition of the substrates and ordered release of the products. The second distinction concerns the inhibitory effect of the acceptor. In the case of alpha-chymotrypsin this was the result of true inhibition, i.e. a dead-end formation of the enzyme-acceptor complex. A salt effect caused by the acceptor was the rationale of a similar effect observed in acyl-transfer catalysed by gamma-glutamyltranspeptidase.

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44

Freitag, Anja, Emmanuel Wemakor, Shu-Ming Li, and Lutz Heide. "Acyl Transfer in Clorobiocin Biosynthesis: Involvement of Several Proteins in the Transfer of the Pyrrole-2-carboxyl Moiety to the Deoxysugar." ChemBioChem 6, no. 12 (2005): 2316–25. http://dx.doi.org/10.1002/cbic.200500252.

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45

Mandai, Hiroki, Kazuki Fujii, and Seiji Suga. "Recent topics in enantioselective acyl transfer reactions with dialkylaminopyridine-based nucleophilic catalysts." Tetrahedron Letters 59, no. 19 (2018): 1787–803. http://dx.doi.org/10.1016/j.tetlet.2018.03.016.

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Chen, Peng, та Jin Qu. "Backbone Modification of β-Hairpin-Forming Tetrapeptides in Asymmetric Acyl Transfer Reactions". Journal of Organic Chemistry 76, № 9 (2011): 2994–3004. http://dx.doi.org/10.1021/jo200403g.

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47

Molander, Gary A., and Christina R. Harris. "Sequential Nucleophilic Acyl Substitution/Alkenyl Transfer Reactions Mediated by Samarium(II) Iodide." Journal of Organic Chemistry 63, no. 13 (1998): 4374–80. http://dx.doi.org/10.1021/jo980184o.

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48

Sibi, Mukund P., Yasutomi Asano та Justin B. Sausker. "Enantioselective Hydrogen Atom Transfer Reactions: Synthesis ofN-Acyl-α-Amino Acid Esters". Angewandte Chemie International Edition 40, № 7 (2001): 1293–96. http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1293::aid-anie1293>3.0.co;2-y.

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49

Sibi, Mukund P., Yasutomi Asano та Justin B. Sausker. "Enantioselective Hydrogen Atom Transfer Reactions: Synthesis ofN-Acyl-α-Amino Acid Esters". Angewandte Chemie 113, № 7 (2001): 1333–36. http://dx.doi.org/10.1002/1521-3757(20010401)113:7<1333::aid-ange1333>3.0.co;2-g.

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50

Kakuchi, Ryohei, Kwanjira Wongsanoh, Voravee P. Hoven, and Patrick Theato. "Activation of stable polymeric esters by using organo-activated acyl transfer reactions." Journal of Polymer Science Part A: Polymer Chemistry 52, no. 9 (2014): 1353–58. http://dx.doi.org/10.1002/pola.27124.

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