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Journal articles on the topic '6- aminopenicillanic acid'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

A., M. AHDEL-HALIM, M. ABDEL-AZIZ R., ABDEL-NASSER G. та I. HASHEM A. "Synthesis of New Derivatives of β-Lactam-containing Antibiotics formed with certain Sulphonyl Chlorides". Journal of Indian Chemical Society Vol. 73, Nov 1996 (1996): 584–86. https://doi.org/10.5281/zenodo.5917630.

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Chemistry Department, Faculty of Education, Ain Shams University, Roxy. Cairo. Egypt Research Department. EI-Nasr Pharmaceutical Chemical Company, Abu Zabal, Egypt Chemistry Department Faculty of Science, Ain-Shams University. Abasia, Cairo, Egypt <em>Manuscript received 17 November 1994. accepted 4 April 1915</em> 6-Aminopenicillanic acid and 7-aminodeacetoxycephalosporanic acid react with a number or sulphonyl chloride derivatives, including 4-acetylaminohenzenesulphonyl  chloride, phenylacetic acid-4-sulphonyl chloride and uracil-5-sulphonyl chloride to form new family of com

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2

Galaction, A. I., M. Postaru, A. Tucaliuc, I. Ungureanu, and D. Cascaval. "Reactive extraction of 6-aminopenicillanic acid." New Biotechnology 44 (October 2018): S138. http://dx.doi.org/10.1016/j.nbt.2018.05.1102.

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3

Veinberg, Grigory, Maxim Vorona, Dan Musel, Nora Grigan, and Edmunds Lukevics. "Preparation of tert-Butyl 6-Aminopenicillanate and its 6-Oxo and 6-Diazo Derivatives." Journal of Chemical Research 23, no. 4 (1999): 270–71. http://dx.doi.org/10.1177/174751989902300412.

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A 1:1 1,4-dioxane– tert-butyl acetate mixture and BF3 etherate were used for an effective 6-aminopenicillanic acid conversion into the tert-butyl ester (64 ± 3% yield) which could be easily transformed into tert-butyl 6-oxo- and 6-diazo-penicillanates.

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4

Stroganov, Oleg V., Ghermes G. Chilov, and Vytas K. Švedas. "Force field parametrization for 6-aminopenicillanic acid." Journal of Molecular Structure: THEOCHEM 631, no. 1-3 (2003): 117–25. http://dx.doi.org/10.1016/s0166-1280(03)00231-8.

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5

Ferreira, Juliana S., Adrie J. J. Straathof, Xiaonan Li, Marcel Ottens, Telma T. Franco, and Luuk A. M. van der Wielen. "Solution Crystallization Kinetics of 6-Aminopenicillanic Acid." Industrial & Engineering Chemistry Research 45, no. 20 (2006): 6740–44. http://dx.doi.org/10.1021/ie0601652.

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6

Galindo, E., F. Lagunas, J. Osuna, X. Soberón, and J. L. Garcı́a. "A microbial biosensor for 6-aminopenicillanic acid." Enzyme and Microbial Technology 23, no. 5 (1998): 331–34. http://dx.doi.org/10.1016/s0141-0229(98)00057-x.

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7

S., D. Gunagi, T. Nandibewoor S., and A. Chimatadar S. "Osmium(VIII) catalysed oxidation of 6-aminopenicillanic acid by diperiodatoargentate( III) in aqueous alkaline medium by stopped flow technique." Journal of Indian Chemical Society Vol. 88, Sep 2011 (2011): 1339–48. https://doi.org/10.5281/zenodo.5787869.

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P.G. Department of Studies in Chemistry, Karnatak University, Dharwad-580 003, Karnataka. India <em>E-mail</em> : schimatadar@gmail.com <em>Manuscript received 06 September 2010, revised 30 December 2010, accepted 30 December 2010</em> The kinetics of micro amounts (10<sup>-7</sup> mol dm<sup>-3</sup>) of osmium(VIII) catalysed oxidation of 6-aminupenicillanic acid by diperiodatoargentate(lll) in alkaline medium at 25 °C and at a constant ionic strength of 0.04 mol dm<sup>-3 </sup>was studied spectrophotometrically. The oxidation products were confirmed by IR, LC-ESI-l\IS and NMR spectral

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8

Fekner, Tomasz, Jack E. Baldwin, Robert M. Adlington, Timothy W. Jones, C. Keith Prout, and Christopher J. Schofield. "Syntheses of (6S)-Cephalosporins from 6-Aminopenicillanic Acid." Tetrahedron 56, no. 33 (2000): 6053–74. http://dx.doi.org/10.1016/s0040-4020(00)00486-5.

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9

Dutta, M., R. Baruah, and N. N. Dutta. "Adsorption of 6-aminopenicillanic acid on activated carbon." Separation and Purification Technology 12, no. 2 (1997): 99–108. http://dx.doi.org/10.1016/s1383-5866(97)00033-6.

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10

Favre, Annack, Jrme Grugier, Alain Brans, Bernard Joris, and Jacqueline Marchand-Brynaert. "6-Aminopenicillanic acid (6-APA) derivatives equipped with anchoring arms." Tetrahedron 68, no. 52 (2012): 10818–26. http://dx.doi.org/10.1016/j.tet.2011.10.100.

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11

Almalki, Atiah H., Essraa A. Hussein, Ibrahim A. Naguib, Eglal A. Abdelaleem, Hala E. Zaazaa, and Fatma F. Abdallah. "Development and Validation of Ecofriendly HPLC-MS Method for Quantitative Assay of Amoxicillin, Dicloxacillin, and Their Official Impurity in Pure and Dosage Forms." Journal of Analytical Methods in Chemistry 2021 (June 17, 2021): 1–9. http://dx.doi.org/10.1155/2021/5570938.

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Novel, accurate, selective, and rapid high-performance liquid chromatography mass spectrometry method was developed for simultaneous analysis of amoxicillin trihydrate, dicloxacillin sodium, and their official impurity 6-aminopenicillanic acid. The chromatographic separation was carried out by applying the mixture on a C18 column (3.5 µm ps, 100 mm × 4.6 mm id) using acetonitrile:water (65 : 35 by volume) as a mobile phase within only 4 min. The quantitative analysis was executed using single quadrupole mass spectrometer in which electrospray ionization, selected ion monitoring, and negative m

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12

Husinec, Suren, Deana Dragović, Zdenka Stokić, and Josipa Kojić. "Some approaches to the synthesis of sulbactam." Collection of Czechoslovak Chemical Communications 54, no. 5 (1989): 1370–75. http://dx.doi.org/10.1135/cccc19891370.

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A study on the synthesis of penicillanic acid 1,1-dioxide, Sulbactam, was carried out. Two reliable convergent synthetic routes to this β-lactamase inhibitor starting from penicillin G potassium salt and 6-aminopenicillanic acid have been developed.

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13

Coulton, Steven, and Irene François. "Synthesis of 6-(substituted methylene) carbapenem derivatives from 6-aminopenicillanic acid." J. Chem. Soc., Perkin Trans. 1, no. 11 (1991): 2699–705. http://dx.doi.org/10.1039/p19910002699.

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14

Maruyama, Hiroshi, and Tetsuo Hiraoka. "A stereocontrolled synthesis of thienamycin from 6-aminopenicillanic acid." Journal of Organic Chemistry 51, no. 3 (1986): 399–402. http://dx.doi.org/10.1021/jo00353a025.

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15

Rolinson, George N. "The influence of 6-aminopenicillanic acid on antibiotic development." Journal of Antimicrobial Chemotherapy 22, no. 1 (1988): 5–14. http://dx.doi.org/10.1093/jac/22.1.5.

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16

Tavare, Narayan S., and Vivek K. Jadhav. "Solubilities of 6-Aminopenicillanic Acid and Phenoxyacetic Acid in Hydrotrope Solutions." Journal of Chemical & Engineering Data 41, no. 5 (1996): 1196–202. http://dx.doi.org/10.1021/je960160j.

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17

Parmar, Anupama, Harish Kumar, S. S. Marwaha, and J. F. Kennedy. "Advances in enzymatic transformation of penicillins to 6-aminopenicillanic acid (6-APA)." Biotechnology Advances 18, no. 4 (2000): 289–301. http://dx.doi.org/10.1016/s0734-9750(00)00039-2.

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18

Rolinson, G. N., and A. M. Geddes. "The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA)." International Journal of Antimicrobial Agents 29, no. 1 (2007): 3–8. http://dx.doi.org/10.1016/j.ijantimicag.2006.09.003.

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19

CASY, A. F., and A. LIPCZYNSKI. "8-Hydroxypenillic acid: NMR characteristics and facile formation from 6-aminopenicillanic acid." Journal of Pharmacy and Pharmacology 46, no. 6 (1994): 533–34. http://dx.doi.org/10.1111/j.2042-7158.1994.tb03848.x.

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20

Mwangi, S. M., and J. Garside. "Morphology of 6-aminopenicillanic acid crystals and the effect of phenoxyacetic acid." Journal of Crystal Growth 166, no. 1-4 (1996): 1078–83. http://dx.doi.org/10.1016/0022-0248(96)00111-x.

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21

Saouane, Sofiane, Gernot Buth, and Francesca P. A. Fabbiani. "Crystal structure and packing energy calculations of (+)-6-aminopenicillanic acid." Acta Crystallographica Section C Crystal Structure Communications 69, no. 11 (2013): 1238–42. http://dx.doi.org/10.1107/s0108270113025924.

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The X-ray single-crystal structure of (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, commonly known as (+)-6-aminopenicillanic acid (C8H12N2O3S) and a precursor of a variety of semi-synthetic penicillins, has been determined from synchrotron data at 150 K. The structure represents an ordered zwitterion and the crystals are nonmerohedrally twinned. The crystal structure is composed of a three-dimensional network built by three charge-assisted hydrogen bonds between the ammonium and carboxylate groups. The complementary analysis of the crystal packing

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22

Weissenburger, H. W. O., and M. G. van der Hoeven. "An efficient nonenzymatic conversion of benzylpenicillin to 6-aminopenicillanic acid." Recueil des Travaux Chimiques des Pays-Bas 89, no. 10 (2010): 1081–84. http://dx.doi.org/10.1002/recl.19700891011.

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23

COULTON, S., and I. FRANCOIS. "ChemInform Abstract: Synthesis of 6-(Substituted Methylene) Carbapenem Derivatives from 6- Aminopenicillanic Acid." ChemInform 23, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199206289.

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24

Fekner, Tomasz, Jack E. Baldwin, Robert M. Adlington, and Christopher J. Schofield. "Syntheses of (6S,7S)- and (6S,7R)-deacetoxycephalosporanic acids from 6-aminopenicillanic acid." Chemical Communications, no. 16 (1996): 1989. http://dx.doi.org/10.1039/cc9960001989.

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25

Suga, Ken-ichi, Tomoko Sorai, Suteaki Shioya, and Fumihiro Ishimura. "Production of 6-Aminopenicillanic Acid in Immobilized Enzyme Reactor with Electrodialysis." JOURNAL OF CHEMICAL ENGINEERING OF JAPAN 26, no. 6 (1993): 709–14. http://dx.doi.org/10.1252/jcej.26.709.

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26

Aguiar, M. R. M. P., S. M. C. Menezes, A. L. Gemal, and R. A. S. San Gil. "Solid-state 13C nuclear magnetic resonance spectra of 6-aminopenicillanic acid." Solid State Nuclear Magnetic Resonance 4, no. 3 (1995): 179–85. http://dx.doi.org/10.1016/0926-2040(94)00044-d.

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27

Shewale, Jaiprakash G., Kamalesh K. Kumar, and Gangadhar R. Ambekar. "Evaluation of determination of 6-aminopenicillanic acid by p-dimethyl aminobenzaldedyde." Biotechnology Techniques 1, no. 1 (1987): 69–72. http://dx.doi.org/10.1007/bf00156291.

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28

Lowe, D. A., G. Romancik, and R. P. Elander. "Enzymatic hydrolysis of penicillin V to 6-aminopenicillanic acid byFusarium oxysporum." Biotechnology Letters 8, no. 3 (1986): 151–56. http://dx.doi.org/10.1007/bf01029369.

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29

Nov�?kov�, J., K. Plh�?kov�, and B. Sikyta. "Sanitization of immobilized biocatalysts for the production of 6-aminopenicillanic acid." Acta Biotechnologica 20, no. 2 (2000): 161–68. http://dx.doi.org/10.1002/abio.370200211.

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30

Sengar, S., S. K. Singh, and M. K. Gupta. "Design and synthesis of iron(II) complexes with Schiff bases derived from 6-aminopenicillanic acid and heterocyclic aldehydes." Research Journal of Chemistry and Environment 26, no. 4 (2022): 163–66. http://dx.doi.org/10.25303/2604rjce163166.

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The reaction of iron (II) acetate with Schiff bases derived from the condensation reaction of benzaldehyde or indole-3-carboxaldehyde with (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1azabi cyclo[3.2.0] hepta -ne-2-carboxylic acid (6- Aminopenicillanic Acid) in 1:1 molar ratio gave a new series of iron(II) complexes. The coordination bond formation behaviour of Schiff bases with iron atom has been characterised by elemental analysis, conductance measurements, molecular weight determinations, IR, UV and 1H NMR spectral studies.

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31

Dubey, Sushil K., та Edward E. Knaus. "Synthesis of heterocyclic 1,4-dihydropyridylacetic acid derivatives of 6-aminopenicillanic acid and D-α-aminobenzylpenicillin with antibacterial activity". Canadian Journal of Chemistry 63, № 3 (1985): 559–64. http://dx.doi.org/10.1139/v85-091.

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Condensation of 4-substituted 3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylacetic acids 3 with the C-2 p-bromophenacyl esters of 6-aminopenicillanic acid salt 4 and D-α-aminobenzylpenicillin 8 afforded the respective 1,4-dihydropyridylacetic acid analogs 6 and 10 which exhibited moderate antibacterial activity toward Gram-positive strains. The 6-APA derivatives 6 exhibited dual 1H nmr resonances for H2′, H2, H5, and one of the C3-Me groups, suggesting the presence of two rotamers which differ in configuration at the carbonyl-to-nitrogen bond. The D-aminobenzylpenicillin derivatives 9 may ex

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32

Tewari, Yadu B., and Robert N. Goldberg. "Thermodynamics of the conversion of penicillin G to phenylacetic acid and 6-aminopenicillanic acid." Biophysical Chemistry 29, no. 3 (1988): 245–52. http://dx.doi.org/10.1016/0301-4622(88)85045-2.

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33

Liu, Hong-min, De-quan Yu, Bin Yu та ін. "The New Convenient Synthesis of Novel γ-Alkylidenebutenolides from 6-Aminopenicillanic Acid". HETEROCYCLES 87, № 1 (2013): 163. http://dx.doi.org/10.3987/com-12-12611.

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34

Shibata, Norio, Matthew D. Lloyd, Jack E. Baldwin, and Christopher J. Schofield. "Adipoyl-6-aminopenicillanic acid is a substrate for deacetoxycephalosporin C synthase (DAOCS)." Bioorganic & Medicinal Chemistry Letters 6, no. 13 (1996): 1579–84. http://dx.doi.org/10.1016/s0960-894x(96)00278-8.

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35

Amin, Alaa S., and Yousry M. Issa. "Spectrophotometric determination of 6-aminopenicillanic acid using bromophenol blue and bromothymol blue." Mikrochimica Acta 117, no. 3-4 (1995): 187–94. http://dx.doi.org/10.1007/bf01244889.

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36

Shewale, Jaiprakash G., and Vayalombron K. Sudhakaran. "Penicillin V acylase: Its potential in the production of 6-aminopenicillanic acid." Enzyme and Microbial Technology 20, no. 6 (1997): 402–10. http://dx.doi.org/10.1016/s0141-0229(96)00176-7.

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37

Nabais, A. M. A., and J. P. Cardoso. "Enzymatic conversion of benzylpenicillin to 6-aminopenicillanic acid in concentrated ultrafiltered broths." Bioprocess Engineering 23, no. 2 (2000): 0191–97. http://dx.doi.org/10.1007/s004499900150.

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38

Bora, M. M., A. C. Ghosh, N. N. Dutta, and R. K. Mathur. "Reactive extraction of 6-aminopenicillanic acid with aliquat-336: Equilibrium and kinetics." Canadian Journal of Chemical Engineering 75, no. 3 (1997): 520–26. http://dx.doi.org/10.1002/cjce.5450750305.

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39

Mandel, Martin, Ludvík Novák, Miroslav Rajšner, Jiří Holubek, and Vladislava Holá. "New synthesis of oxime-type beta-lactam antibiotics." Collection of Czechoslovak Chemical Communications 54, no. 6 (1989): 1734–45. http://dx.doi.org/10.1135/cccc19891734.

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Reaction of anhydrous acids II with phosphorus pentachloride afforded hydrochlorides of chlorides III which were used in acylations of N,O-bis(trimethylsilyl) derivatives of 6-aminopenicillanic and 7-aminodeacetoxycephalosporanic acid. Change of the (Z)-configuration of the alkoxyimino group during the synthesis was observed only in the methoxyimino series. The prepared penicillins IV are effective against gram-positive as well as gram-negative bacteria.

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40

Lakaye, B., C. Damblon, M. Jamin, et al. "Synthesis, purification and kinetic properties of fluorescein-labelled penicillins." Biochemical Journal 300, no. 1 (1994): 141–45. http://dx.doi.org/10.1042/bj3000141.

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The synthesis and properties of six fluorescein-labelled penicillins are reported. The two isomers of fluoresceyl-glycyl-6-amino-penicillanic acid are probably the best compounds to use for detection of all the penicillin-binding proteins (PBPs) present in a bacterial membrane preparation. However, the derivatives of ampicillin were much more efficient against Enterobacter aerogenes PBP3. The two isomers obtained when a commercial mixture of the two isomers of carboxyfluorescein was used most often exhibited similar properties, but the Streptomyces R61 extracellular DD-peptidase was only effic

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41

Torres-Bacete, Jesús, Miguel Arroyo, Raquel Torres-Guzmán, Isabel de la Mata, María Pilar Castillón, and Carmen Acebal. "Optimization of 6-aminopenicillanic acid (6-APA) production by using a new immobilized penicillin acylase." Biotechnology and Applied Biochemistry 32, no. 3 (2000): 173. http://dx.doi.org/10.1042/ba20000042.

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42

Barrett, Anthony G. M., and Santi Sakadarat. "Total syntheses of penicillanic acid S,S-dioxide and 6-aminopenicillanic acid using (benzyloxy)nitromethane." Journal of Organic Chemistry 55, no. 17 (1990): 5110–17. http://dx.doi.org/10.1021/jo00304a024.

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43

CHEN, DONG-HWANG, SUNG-SHYONG WANG, and TING-CHIA HUANG. "Separation of Phenylacetic Acid, 6-Aminopenicillanic Acid, and Penicillin G with Electrodialysis under Constant Voltage." Separation Science and Technology 31, no. 6 (1996): 839–56. http://dx.doi.org/10.1080/01496399608001328.

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44

Chen, Dong-Hwang, Sung-Shyong Wang, and Ting-Chia Huang. "Separation of phenylacetic acid, 6-aminopenicillanic acid and penicillin G with electrodialysis under constant current." Journal of Chemical Technology AND Biotechnology 64, no. 3 (1995): 284–92. http://dx.doi.org/10.1002/jctb.280640311.

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45

FEKNER, T., J. E. BALDWIN, R. M. ADLINGTON, and C. J. SCHOFIELD. "ChemInform Abstract: Syntheses of (6S,7S)- and (6S,7R)-Deacetoxycephalosporanic Acids from 6-Aminopenicillanic Acid." ChemInform 27, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199648262.

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46

Whiteman, P. A., E. P. Abraham, J. E. Baldwin, et al. "Acyl coenzyme A: 6-aminopenicillanic acid acyltransferase from Penicillium chrysogenum and Aspergillus nidulans." FEBS Letters 262, no. 2 (1990): 342–44. http://dx.doi.org/10.1016/0014-5793(90)80224-7.

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47

Haginaka, Jun, and Junko Wakai. "High-performance liquid chromatographic determination of 6-aminopenicillanic acid by postcolumn alkaline degradation." Analytical Biochemistry 158, no. 1 (1986): 146–50. http://dx.doi.org/10.1016/0003-2697(86)90602-0.

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48

Shehata, M. R., M. M. Shoukry, and M. H. Barakat. "Coordination properties of 6-aminopenicillanic acid: binary and ternary complexes involving biorelevant ligands." Journal of Coordination Chemistry 57, no. 16 (2004): 1369–86. http://dx.doi.org/10.1080/0095897042000261935.

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49

Aguiar, Daniel Lima Marques de, Rosane Aguiar da Silva San Gil, Ricardo Bicca de Alencastro, et al. "6-Aminopenicillanic acid revisited: A combined solid state NMR and in silico refinement." Chemical Physics Letters 660 (September 2016): 214–20. http://dx.doi.org/10.1016/j.cplett.2016.08.030.

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50

Banville, Jacques, Philippe Lapointe, Bernard Belleau та Marcel Menard. "Nuclear analogs of β-lactam antibiotics. Synthesis of 6,6-disubstituted acylaminopenems". Canadian Journal of Chemistry 66, № 6 (1988): 1390–99. http://dx.doi.org/10.1139/v88-225.

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The preparation of 6α-methyl-2-methyl-6β-phenoxyacetamidopenem-3-carboxylate, 6α-methoxy-2-methyl-6β-phenoxyacetamidopenem-3-carboxylate, and 6α-methoxy-2-methyl-6β-phenylmalonylamidopenem-3-carboxylate from penicillin V and 6-aminopenicillanic acid is described. These penems have been isolated and characterized as their sodium or potassium salt. The chemical stability of the above compounds was determined as their half-life in aqueous buffer. In this way, it was found that the 6α-methyl analog was more stable than the parent 6-monosubstituted acylaminopenem while the remaining analogs were of

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