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Journal articles on the topic 'Azido sugar'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Kumar, Manish, Rajesh Kumar, Neha Rana, and Ashok K. Prasad. "Chemo-enzymatic Synthesis of 3′-azido/-amino-C-4′-spirooxetano-xylo nucleosides." Current Green Chemistry 7, no. 1 (2020): 120–27. http://dx.doi.org/10.2174/2213346107666200110092413.

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Conformationally locked 3&#039;-azido-C-4&#039;-spirooxetano-xylonucleosides T, U, C and A have been synthesized by following chemo-enzymatic convergent route. One of the 3&#039;-azido-C-4&#039;- spirooxetano-xylonucleosides, i.e. T was converted into 3&#039;-amino-C-4&#039;-spirooxetano-xylothymidine by reduction of azide to amine with H2/Pd-C in ethyl acetate in quantitative yield. The crucial step in the synthesis of spirooxetano-xylonucleosides is the Lipozyme® TL IM-mediated exclusive diastereoselective acetylation of 4-C-hydroxymethyl group in dihydroxysugar deriv

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2

Krečmerová, Marcela, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "2',3'-Dideoxy- and 3'-Azido-2',3'-dideoxynucleosides of 5-Phenyl-2(1H)-pyrimidinone. Preparation of 2',3'-Dideoxypentofuranoses." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 478–88. http://dx.doi.org/10.1135/cccc19960478.

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The synthesis of methyl 3-azido-5-benzoyl-2,3-dideoxy-β-D-ribofuranoside (10) from methyl 2-deoxy-D-ribofuranoside (1) and its use for the preparation of 3'-azido-2',3'-dideoxy-β-D-ribofuranosides is described. Reaction of methylglucoside 1 with benzoyl chloride in pyridine afforded 5-O-benzoyl derivative 2, which on oxidation with complex of chromium trioxide, pyridine and acetic anhydride afforded 3-keto derivative 3. This was reduced with sodium borohydride in ethanol to give a mixture of methyl 2-deoxyglycosides of α-D-ribo- (4) and β-D-xylo- (5) configuration. Their mesyl derivatives 6 an

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3

Chhikara, Bhupender S., M. Sudershan Rao, V. Kameshwara Rao, et al. "Carbocyclodipeptides as modified nucleosides: synthesis and anti-HIV activities." Canadian Journal of Chemistry 92, no. 12 (2014): 1145–49. http://dx.doi.org/10.1139/cjc-2014-0356.

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A new class of nucleoside analogues were synthesized using cyclic dipeptides and modified 2′-deoxyfuranoribose sugars to introduce flexibility by peptides in place of common nucleoside bases and to determine their biological properties. The synthesis was carried out by coupling of a protected ribose sugar with synthesized dipeptides in the presence of hexamethyldisilazane and trimethylsilyltriflate. The final products were characterized by NMR and high-resolution MS-TOF spectroscopy. The compounds were evaluated for anti-HIV activities. 1-(4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6-dii

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4

Zsoldos-Mády, Virág, István Pintér, Péter Sándor, and András Messmer. "New imino sugar derivatives from a 6-azido-6-deoxy sugar formazan." Carbohydrate Research 281, no. 2 (1996): 321–26. http://dx.doi.org/10.1016/0008-6215(95)00352-5.

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5

MarcoContelles, José, Nadine Jagerovic та C. Alhambra. "1,3-Dipolar Cycloaddition of 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose and C60". Journal of Chemical Research 23, № 11 (1999): 680–81. http://dx.doi.org/10.1177/174751989902301122.

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6

Zeid, Ibrahim F., and Adel A. H. Abdel-Rahman. "Synthesis of 2-O-Ethyl Analogues of 5′-Azido- and 5′-Amino-2’,5′-dideoxyuridines as New Antiviral Agents." Journal of Chemical Research 23, no. 3 (1999): 192–93. http://dx.doi.org/10.1177/174751989902300311.

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2- O-Ethyluracil derivatives 3a-d have been silylated with HMDS and condensed in the presence of TMS-triflate with a 5-azido sugar to give the corresponding β-nucleosides 5a-d and their α-anomers 6a-d; deprotection afforded 7 and 8, and the 5′-amino derivatives 9a,b could be obtained by treatment of the corresponding 5′-azido nucleosides with triphenylphosphine in pyridine.

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7

Ren, Yiqian, Yao Qiang, Xinrui Duan, and Zhengping Li. "The distinct difference in azido sugar metabolic rate between neural stem cells and fibroblasts and its application for decontamination of chemically induced neural stem cells." Chemical Communications 56, no. 15 (2020): 2344–47. http://dx.doi.org/10.1039/c9cc09362a.

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8

ZSOLDOS-MADY, V., I. PINTER, P. SANDOR, and A. MESSMER. "ChemInform Abstract: New Imino Sugar Derivatives from a 6-Azido-6-deoxy Sugar Formazan." ChemInform 27, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199624219.

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9

Mishra, Kunj B., Somesh Shashi, and Vinod K. Tiwari. "Metal free synthesis of morpholine fused [5,1-c] triazolyl glycoconjugates via glycosyl azido alcohols." RSC Advances 5, no. 105 (2015): 86840–48. http://dx.doi.org/10.1039/c5ra17181d.

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A series of diverse glycosyl 1,2-azido alcohols, obtained from readily available carbohydrates, were converted to structurally varied rare and novel sugar derived morpholine fused [5,1-c]-triazoles via a one-pot strategy.

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10

Wainman, Yéléna A., André A. Neves, Shaun Stairs, et al. "Dual-sugar imaging using isonitrile and azido-based click chemistries." Organic & Biomolecular Chemistry 11, no. 42 (2013): 7297. http://dx.doi.org/10.1039/c3ob41805g.

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11

Chennaiah, Ande, Srijita Bhowmick, and Yashwant D. Vankar. "Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of N-glycopeptides, pseudo-trisaccharides and an iminosugar." RSC Advances 7, no. 66 (2017): 41755–62. http://dx.doi.org/10.1039/c7ra08637g.

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Glycals react with PIFA (or PIDA)–TMSN<sub>3</sub>in presence of TMSOTf to form sugar derived 1,2-diazides and vicinal azidoacetates. Synthesis of 2-azido-N-glycopeptides, pseudotrisaccharides, and a piperidine triol derivative is reported.

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12

González, G., M. Pérez, I. Santana, et al. "Mutagenic activity of 3-azido-1,2-propanediol and sodium azide applied to sugar cane callus cells." Biologia Plantarum 32, no. 5 (1990): 388–90. http://dx.doi.org/10.1007/bf02898505.

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13

J. F. S. da Silva, Anderson, Jucleiton J. R. de Freitas, Silvia M. de Souza та ін. "Synthesis and Cytotoxic Activity of New Alkyl 2-Azido-2,3-Dideoxy-α-D-Lixo-Hexopyranosides From α,β-Unsaturated Sugar Enones and Sodium Azide". Revista Virtual de Química 11, № 6 (2019): 1823–34. http://dx.doi.org/10.21577/1984-6835.20190127.

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14

Alaoui, A. M. El, A. Faraj, C. Pierra та ін. "Inhibition of Hepatitis B Virus Replication by Nucleoside Enantiomers of β-2′,3′-Dideoxypurine Analogues". Antiviral Chemistry and Chemotherapy 7, № 5 (1996): 276–80. http://dx.doi.org/10.1177/095632029600700508.

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Various purine β-L-2′,3′-dideoxynucleoside analogues with both sugar and base modifications including β-L-ddG, β-L-ddl, β-L-ddA, 2′-azido-β-L-araddA, 2′-amino-β-L-araddA, 2′,5′-anhydro-β-L-araddA, 2′-azido-β-L-ddA, 2′-amino-β-L-ddA, 2′-fluoro-β-L-ddA, 3′-azido-β-L-ddA, 3′-amino-β-L-ddA, 3′-fluoro-β-L-ddA, 2,6-diamino-β-L-2′,3′-dideoxyfuranosylpurine, 6-cyclopropylamino-β-L-ddA, 2′-azido-6-N-triphenylphosphine-β-L-araddA, 2-amino-6-methylamino-β-L-2′,3′-dideoxyfuranosylpurine, 2-amino-6-cyclopropylamino-β-L-2′,3′-dideoxyfuranosylpurine, 2-amino-6-cyclopentylamino-β-L-2′,3′-dideoxyfuranosylpurin

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15

Liu, Jiang, Peter Leonard, Sebastian L. Müller, Constantin Daniliuc, and Frank Seela. "Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains." Beilstein Journal of Organic Chemistry 14 (September 13, 2018): 2404–10. http://dx.doi.org/10.3762/bjoc.14.217.

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Copper(I)-promoted "click" cyclization in the presence of TBTA afforded nucleoside macrocycles in very high yields (≈70%) without using protecting groups. To this end, dU and dC derivatives functionalized at the 5-position of the nucleobase with octadiynyl side chains and with azido groups at the 5’-position of the sugar moieties were synthesized. The macrocycles display freely accessible Watson–Crick recognition sites. The conformation of the 16-membered macrocycle was deduced from X-ray analysis and 1H,1H-NMR coupling constants. The sugar conformation (N vs S) was different in solution as co

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16

Peri, Francesco, Laura Cipolla, Barbara La Ferla, and F. Nicotra. "Synthesis of bicyclic sugar azido acids and their incorporation in cyclic peptides." Chemical Communications, no. 23 (2000): 2303–4. http://dx.doi.org/10.1039/b006192l.

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17

Journal, Baghdad Science. "Synthesis and Characterization of Some New Nucleoside Analogues from Substituted Benzimidazole via 1,3-Dipolar cycloaddition." Baghdad Science Journal 13, no. 2 (2016): 298–306. http://dx.doi.org/10.21123/bsj.13.2.298-306.

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This paper includes the synthesis of some new nucleoside analogues starting with 2-substituted benzimidazole derivative (7-9), that synthesized by condensation of O-phenylenediamine with p-chloro benzaldehyde and two substituted benzoic acid , which on nucleophilic substitution with propargyl bromide gave a new N-substituted compounds (10-12). D-Fructose and D-galactose were chosen as a sugar moiety which were protected, brominated and azotated to give azido sugars (5) and (6), then they were subjected to 1,3-dipolar cycloaddition reaction with N-substuted compounds afforded bloked nucleoside

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18

Robins, Morris J., Ruiming Zou, Fritz Hansske, and Stanislaw F. Wnuk. "Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymatic deamination with adenosine deaminase." Canadian Journal of Chemistry 75, no. 6 (1997): 762–67. http://dx.doi.org/10.1139/v97-092.

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Treatment of 2,6-diaminopurine riboside (2-aminoadenosine) with α-acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2′,3′-bromohydrin acetates 2. Treatment of 2 with zinc–copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a). Treatment of 2 with Dowex 1 × 2 (OH−) resin in methanol gave the 2′,3′-anhydro derivative 4. Stannyl radical-mediated hydrogenolysis of 2 and deprotection gave the 2′-deoxy 6a and 3′-deoxy 7a nucleosides. Treatment of the 3′,5′-O-(tetraisopropyldisiloxanyl) derivative (

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19

Czifrák, Katalin, Péter Szilágyi та László Somsák. "Anomeric α-azido acid (2-azido-2-deoxy-hept-2-ulopyranosonic acid) derivatives en route to peptides incorporating sugar amino acids". Tetrahedron: Asymmetry 16, № 1 (2005): 127–41. http://dx.doi.org/10.1016/j.tetasy.2004.11.064.

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20

Zamyatina, Alla, Ralph Hollaus, Markus Blaukopf, and Paul Kosma. "Synthesis of lipid A and inner-core lipopolysaccharide (LPS) ligands containing 4-amino-4-deoxy-L-arabinose units." Pure and Applied Chemistry 84, no. 1 (2011): 11–21. http://dx.doi.org/10.1351/pac-con-11-08-01.

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Attachment of 4-amino-4-deoxy-L-arabinose (Ara4N) to phosphates or sugar hydroxyl groups of lipopolysaccharide (LPS) contributes to bacterial resistance against common antibiotics. For a detailed study of antigenic properties and binding interactions, Ara4N-containing inner-core ligands related to Burkholderia and Proteus LPS have been synthesized in good yields. Glycosylation at position 8 of allyl glycosides of oct-2-ulosonic acids (Ko, Kdo) has been accomplished using an N-phenyltrifluoroacetimidate 4-azido-4-deoxy-L-arabinosyl glycosyl donor followed by azide reduction and global deprotect

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21

Misra, Anup Kumar, Arin Gucchait, and Monalisa Kundu. "Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose." Synthesis 53, no. 19 (2021): 3613–20. http://dx.doi.org/10.1055/s-0037-1610777.

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AbstractA pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using a sequential stereoselective glycosylation strategy. A suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used in the stereoselective glycosylation reaction. Functionalized monosaccharide intermediates were prepared judiciously and stereoselectively assembled to get the desired pentasaccharide derivative in excellent

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22

Peri, Francesco, Laura Cipolla, Barbara La Ferla, and F. Nicotra. "ChemInform Abstract: Synthesis of Bicyclic Sugar Azido Acids and Their Incorporation in Cyclic Peptides." ChemInform 32, no. 14 (2001): no. http://dx.doi.org/10.1002/chin.200114201.

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23

Roper, Stephen M., Marina Zemskova, Benjamin A. Neely, et al. "Targeted glycoprotein enrichment and identification in stromal cell secretomes using azido sugar metabolic labeling." PROTEOMICS - Clinical Applications 7, no. 5-6 (2013): 367–71. http://dx.doi.org/10.1002/prca.201300006.

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24

Timmer, Mattie S. M., Steven H. L. Verhelst, Gijsbert M. Grotenbreg, Mark Overhand, and Herman S. Overkleeft. "Carbohydrates as versatile platforms in the construction of small compound libraries." Pure and Applied Chemistry 77, no. 7 (2005): 1173–81. http://dx.doi.org/10.1351/pac200577071173.

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This paper presents our recent results concerning the use of carbohydrates as cheap, chiral, and enantiopure starting materials in the construction of a variety of densely functionalized molecules. The compatibility of ring-closing metathesis with standard carbohydrate chemistry is demonstrated in the synthesis of new stereoisomers of deoxystreptamine and neamine–important building blocks for the generation of synthetic aminoglycosides with potential antibacterial activity. Ring-closing metathesis is also a key step in the rapid synthesis of new indolizidines and quinolizidines, and in a new s

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25

Mishra, Kunj B., Anand K. Agrahari, and Vinod K. Tiwari. "One-pot synthesis of oxazolidine-2-thione and thiozolidine-2-thione from sugar azido-alcohols." Carbohydrate Research 450 (October 2017): 1–9. http://dx.doi.org/10.1016/j.carres.2017.08.002.

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26

del Solar, Virginia, Rohitesh Gupta, Yusen Zhou, Gabrielle Pawlowski, Khushi L. Matta, and Sriram Neelamegham. "Robustness in glycosylation systems: effect of modified monosaccharides, acceptor decoys and azido sugars on cellular nucleotide-sugar levels and pattern of N-linked glycosylation." Molecular Omics 16, no. 4 (2020): 377–86. http://dx.doi.org/10.1039/d0mo00023j.

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Chemical perturbation studies reveal robustness in glycosylation systems, based on comparison of LC-MS/MS quantification of cellular nucleotide-sugar levels with the observed N-linked glycan patterns.

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27

Maciej-Hulme, Marissa L., Eamon Dubaissi, Chun Shao, et al. "Selective Inhibition of Heparan Sulphate and Not Chondroitin Sulphate Biosynthesis by a Small, Soluble Competitive Inhibitor." International Journal of Molecular Sciences 22, no. 13 (2021): 6988. http://dx.doi.org/10.3390/ijms22136988.

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The glycosaminoglycan, heparan sulphate (HS), orchestrates many developmental processes. Yet its biological role has not yet fully been elucidated. Small molecule chemical inhibitors can be used to perturb HS function and these compounds provide cheap alternatives to genetic manipulation methods. However, existing chemical inhibition methods for HS also interfere with chondroitin sulphate (CS), complicating data interpretation of HS function. Herein, a simple method for the selective inhibition of HS biosynthesis is described. Using endogenous metabolic sugar pathways, Ac4GalNAz produces UDP-G

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28

Poznanski, Jaroslaw, Maria Bretner, Tadeusz Kulikowski, Jan Balzarini, Arthur Van Aerschot, and Erik De Clercq. "Synthesis, Solution Conformation and Anti-HIV Activity of Novel 3-Substituted-2′,3′-Dideoxy-5-Hydroxymethyl-Uridines and Their 4,5-Substituted Analogues." Antiviral Chemistry and Chemotherapy 14, no. 3 (2003): 127–38. http://dx.doi.org/10.1177/095632020301400302.

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To decrease the toxicity of potent anti-HIV nucleosides 3-azido-2′,3′-dideoxythymidine (AZT) and 2,3′-dideoxy-3′-fluorothymidine (3-FddThd, FLT), their new analogues, 3-azido-2′,3′-dideoxy-5-hydroxymethyluridine (3-Az5HmddUrd) and 2,3′-dideoxy-3′-fluoro-5-hydroxymethyluridine (3′-F5HmddUrd), were synthesized. The reaction of 3′-azido-2′,3′-dideoxyuridine (3′-AzddUrd) and 2,3′-dideoxy-3′-fluorouridine (3′-FddUrd) with formaldehyde, under strongly alkaline conditions and at elevated temperature, proceeded after 4 days to completion to afford the corresponding 5-hydroxymethyl derivatives 3′-Az5Hm

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29

Robins, Morris J., S. D. Hawrelak, Amelia E. Hernández, and Stanislaw F. Wnuk. "Nucleic Acid Related Compounds. LXXXI. Efficient General Synthesis of Purine (Amino, Azido, and Triflate)-Sugar Nucleosides." Nucleosides and Nucleotides 11, no. 2-4 (1992): 821–34. http://dx.doi.org/10.1080/07328319208021743.

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30

Parang, K., LI Wiebe, and EE Knaus. "Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus." Antiviral Chemistry and Chemotherapy 8, no. 5 (1997): 417–27. http://dx.doi.org/10.1177/095632029700800504.

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A series of 5′- Oacyl derivatives of thymidine (dThd) were prepared by direct acylation of thymidine using the Mitsunobu reaction. Further reaction of the bromo analogues with sodium azide gave azido ester analogues. Anti-human immunodeficiency virus type 1 (HIV-1) activities were determined against HIV-infected T4 lymphocytes. 5′- O-(12-Azidododecanoyl)thymidine exhibited moderate activity (EC50 4.6 μM) against HIV-infected T4 lymphocytes. 5- O-(2-Bromotetradecanoyl)-thymidine was found to be the most stable ester (t1/2 15.3 min) to hydrolysis by porcine liver esterase in vitro. Partition coe

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31

Bo, Yang, Yunjiang Jiang, Kangmei Chen, et al. "Targeting infected host cells in vivo via responsive azido-sugar mediated metabolic cell labeling followed by click reaction." Biomaterials 238 (April 2020): 119843. http://dx.doi.org/10.1016/j.biomaterials.2020.119843.

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32

Sehad, Celia, Tze Shiao, Lamyaa Sallam, Abdelkrim Azzouz, and René Roy. "Effect of Dendrimer Generation and Aglyconic Linkers on the Binding Properties of Mannosylated Dendrimers Prepared by a Combined Convergent and Onion Peel Approach." Molecules 23, no. 8 (2018): 1890. http://dx.doi.org/10.3390/molecules23081890.

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An efficient study of carbohydrate-protein interactions was achieved using multivalent glycodendrimer library. Different dendrimers with varied peripheral sugar densities and linkers provided an arsenal of potential novel therapeutic agents that could be useful for better specific action and greater binding affinities against their cognate protein receptors. Highly effective click chemistry represents the basic method used for the synthesis of mannosylated dendrimers. To this end, we used propargylated scaffolds of varying sugar densities ranging from 2 to 18 for the attachment of azido mannop

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33

Cheng, Janice M. H., Emma M. Dangerfield, Mattie S. M. Timmer, and Bridget L. Stocker. "A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate." Org. Biomol. Chem. 12, no. 17 (2014): 2729–36. http://dx.doi.org/10.1039/c4ob00241e.

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34

Xie, Juan. "Synthesis of Sugar Azido or Amino Esters and Their Use as Building Blocks for the Preparation of Saccharide Nucleosides." European Journal of Organic Chemistry 2002, no. 20 (2002): 3411–18. http://dx.doi.org/10.1002/1099-0690(200210)2002:20<3411::aid-ejoc3411>3.0.co;2-q.

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35

Jin, Yun-Ho, Min Bae, Young-Joo Byun, Joong Hyup Kim, and Moon Woo Chun. "Synthesis and antiviral activity of fluoro sugar nucleosides 1: Studies on 4′-azido-2′-deoxy-2′-fluoro-arabinofuranosyl nucleosides." Archives of Pharmacal Research 18, no. 5 (1995): 364–65. http://dx.doi.org/10.1007/bf02976334.

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36

Maeda, Naoyoshi, Akira Matsuda, Satoko Otsuguro, Masahiko Takahashi, Masahiro Fujii, and Katsumi Maenaka. "Antitumor Effect of Sugar-Modified Cytosine Nucleosides on Growth of Adult T-Cell Leukemia Cells in Mice." Vaccines 8, no. 4 (2020): 658. http://dx.doi.org/10.3390/vaccines8040658.

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Adult T-cell leukemia (ATL) is a CD4+ T-cell neoplasm caused by human T-cell leukemia virus type I. As the prognosis for patients with ATL remains extremely poor due to resistance to conventional chemotherapy regimens, introduction of novel therapeutic agents is needed. Previous studies have reported that nucleosides 2′-deoxy-2′-methylidenecytidine (DMDC) and its derivative 2′-deoxy-2′-methylidene-5-fluorocytidine (FDMDC) exhibit antitumor activities in T-cell acute lymphoblastic leukemia (T-ALL) and solid tumor cell lines. Another nucleoside, 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)cytosine (

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37

Birnbaum, George I., Jerzy Giziewicz, Eric J. Gabe, Tai-Shun Lin, and William H. Prusoff. "Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus." Canadian Journal of Chemistry 65, no. 9 (1987): 2135–39. http://dx.doi.org/10.1139/v87-356.

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3′-Azido-3′-deoxythymidine (AZT), an inhibitor of HIV (human immunodeficiency virus) replication, was recently found to improve the condition of patients suffering from AIDS (acquired immunodeficiency syndrome) or ARC (AIDS-related complex). An X-ray analysis of AZT was undertaken in order to determine the three-dimensional structure of this thymidine analogue. The crystals belong to the monoclinic space group P21 and the cell dimensions are a = 5.6282(4), b = 12.0130(7), c = 17.5072(10) Å, β = 95.946(5)°. The structure was determined by direct methods and refined to R = 0.028 for 2029 observe

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38

Norris, Peter, Derek Horton, and Dasha E. Giridhar. "Intramolecular 1,3-dipolar cycloadditions of 5-azido-5-deoxyaldopentose ketene dithioacetal bis(sulfones) in the synthesis of imino sugar analogs." Tetrahedron Letters 37, no. 23 (1996): 3925–28. http://dx.doi.org/10.1016/0040-4039(96)00716-2.

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39

Sun, Lingbo, Hongxia Fu, Yanru Li, Xinrui Duan, and Zhengping Li. "Rapid Recognition and Isolation of Live Colon Cancer Stem Cells by Using Metabolic Labeling of Azido Sugar and Magnetic Beads." Analytical Chemistry 88, no. 7 (2016): 3953–58. http://dx.doi.org/10.1021/acs.analchem.6b00154.

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40

Hsieh, Yu-Chi, Jiun-Ly Chir, Wei Zou, Hsiu-Han Wu, and An-Tai Wu. "Convenient approaches to synthesis of furanoid sugar-aza-crown ethers from C-ribosyl azido aldehyde via a reductive amination/amidation." Carbohydrate Research 344, no. 8 (2009): 1020–23. http://dx.doi.org/10.1016/j.carres.2009.03.008.

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41

Kapeller, H., та H. Griengl. "Synthesis of methyl 5-azido-5-deoxy-2,3-O-isopropylidenecarba-α-D-allo-hexafuranuronate, the sugar part of carbapolyoxins and carbanikkomycins". Tetrahedron 53, № 43 (1997): 14635–44. http://dx.doi.org/10.1016/s0040-4020(97)01042-9.

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Moni, Lisa, Alessia Ciogli, Ilaria D'Acquarica, Alessandro Dondoni, Francesco Gasparrini, and Alberto Marra. "Synthesis of Sugar-Based Silica Gels by Copper-Catalysed Azide-Alkyne Cycloaddition via a Single-Step Azido-Activated Silica Intermediate and the Use of the Gels in Hydrophilic Interaction Chromatography." Chemistry - A European Journal 16, no. 19 (2010): 5712–22. http://dx.doi.org/10.1002/chem.201000106.

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Mudgal, Mukesh, Thao P. Dang, Adam J. Sobczak, et al. "Site of Azido Substitution in the Sugar Moiety of Azidopyrimidine Nucleosides Influences the Reactivity of Aminyl Radicals Formed by Dissociative Electron Attachment." Journal of Physical Chemistry B 124, no. 50 (2020): 11357–70. http://dx.doi.org/10.1021/acs.jpcb.0c08201.

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44

NORRIS, P., D. HORTON, and D. E. GIRIDHAR. "ChemInform Abstract: Intramolecular 1,3-Dipolar Cycloadditions of 5-Azido-5- deoxyaldopentose Ketene Dithioacetal Bis(sulfones) in the Synthesis of Imino Sugar Analogues." ChemInform 27, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199639232.

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45

Wengel, Jesper, та Erik B. Pedersen. "Selective Deformylation of an α,β-Unsaturated Sugar Aldehyde in a Very Short Synthesis of 3′-Azido-3′-deoxythymidine (AZT) and its Stereoisomers". Synthesis 1991, № 06 (1991): 451–54. http://dx.doi.org/10.1055/s-1991-26490.

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46

KAPELLER, H., та H. GRIENGL. "ChemInform Abstract: Synthesis of Methyl 5-Azido-5-deoxy-2,3-O-isopropylidenecarba-α-D-allo-hexafuranuronat e, the Sugar Part of Carbapolyoxins and Carbanikkomycins." ChemInform 29, № 8 (2010): no. http://dx.doi.org/10.1002/chin.199808199.

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Lennerstrand, Johan, Chung K. Chu та Raymond F. Schinazi. "Biochemical Studies on the Mechanism of Human Immunodeficiency Virus Type 1 Reverse Transcriptase Resistance to 1-(β-d-Dioxolane)Thymine Triphosphate". Antimicrobial Agents and Chemotherapy 51, № 6 (2007): 2078–84. http://dx.doi.org/10.1128/aac.00119-07.

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ABSTRACT A large panel of drug-resistant mutants of human immunodeficiency virus type 1 reverse transcriptase (RT) was used to study the mechanisms of resistance to 1-(β-d-dioxolane)thymine triphosphate (DOT-TP) and other nucleotide analogs. RT containing thymidine analog-associated mutations (TAM) or RT with a T69S-SG insertion in combination with TAM removed 3′-azido-3′-deoxythymidine-5′-monophosphate or tenofovir more efficiently than DOT-monophosphate from chain-terminated DNA primer/template through ATP-mediated pyrophosphorolysis. For non-ATP-dependent discrimination toward DOT-TP, high

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Grymel, Mirosława, Gabriela Pastuch-Gawołek, Anna Lalik, et al. "Glycoconjugation of Betulin Derivatives Using Copper-Catalyzed 1,3-Dipolar Azido-Alkyne Cycloaddition Reaction and a Preliminary Assay of Cytotoxicity of the Obtained Compounds." Molecules 25, no. 24 (2020): 6019. http://dx.doi.org/10.3390/molecules25246019.

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Pentacyclic lupane-type triterpenoids, such as betulin and its synthetic derivatives, display a broad spectrum of biological activity. However, one of the major drawbacks of these compounds as potential therapeutic agents is their high hydrophobicity and low bioavailability. On the other hand, the presence of easily transformable functional groups in the parent structure makes betulin have a high synthetic potential and the ability to form different derivatives. In this context, research on the synthesis of new betulin derivatives as conjugates of naturally occurring triterpenoid with a monosa

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WENGEL, J., та E. B. PEDERSEN. "ChemInform Abstract: Selective Deformylation of an α,β-Unsaturated Sugar Aldehyde in a Very Short Synthesis of 3′-Azido-3′-deoxythymidine (AZT) and Its Stereoisomers." ChemInform 22, № 46 (2010): no. http://dx.doi.org/10.1002/chin.199146300.

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Fürniss, Daniel, Timo Mack, Frank Hahn, et al. "Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry." Beilstein Journal of Organic Chemistry 9 (January 10, 2013): 56–63. http://dx.doi.org/10.3762/bjoc.9.7.

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Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six

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