Dissecting the Influence of Oxazolidinones and Cyclic Carbonates in Sialic Acid Chemistry

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2012 Sep 15

PMID 22976809

Citations 18

Authors

Pavan K Kancharla

Chandrasekhar Navuluri

David Crich

Affiliations

Soon will be listed here.

Abstract

At a moment's notice: Thermal equilibration of 1 and mass spectral analysis of sialyl phosphates suggest that the 4O,5N-oxazolidinone and the 4,5-O-carbonate systems influence the anomeric effect and the mechanisms of sialidation by virtue of their dipole moment in the mean plane of the pyranose ring. The electron-withdrawing effect destabilizes 2 and promotes associative glycosylation mechanisms. TEMPO = 2,2,6,6-tetramethylpiperidine N-oxide.

Citing Articles

Visible-light-promoted direct desulfurization of glycosyl thiols to access C-glycosides.

Xie D, Zeng W, Yang J, Ma X Nat Commun. 2024; 15(1):9187.

PMID: 39448612 PMC: 11502824. DOI: 10.1038/s41467-024-53563-0.

Characterization of Elusive Reaction Intermediates Using Infrared Ion Spectroscopy: Application to the Experimental Characterization of Glycosyl Cations.

Ter Braak F, Elferink H, Houthuijs K, Oomens J, Martens J, Boltje T Acc Chem Res. 2022; 55(12):1669-1679.

PMID: 35616920 PMC: 9219114. DOI: 10.1021/acs.accounts.2c00040.

Synthesis of -acyl furanosides the cross-coupling of glycosyl esters with carboxylic acids.

Wei Y, Lam J, Diao T Chem Sci. 2021; 12(34):11414-11419.

PMID: 34667550 PMC: 8447929. DOI: 10.1039/d1sc03596g.

Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.

Ogasahara R, Abdullayev S, Sarpe V, Mandhapati A, Crich D Carbohydr Res. 2020; 496:108100.

PMID: 32755675 PMC: 7484008. DOI: 10.1016/j.carres.2020.108100.

Synthesis of an Aminooxy Derivative of the GM3 Antigen and Its Application in Oxime Ligation.

Kleski K, Shi M, Lohman M, Hymel G, Gattoji V, Andreana P J Org Chem. 2020; 85(24):16207-16217.

PMID: 32320231 PMC: 7606269. DOI: 10.1021/acs.joc.0c00320.

References

Gu Z, Zhang J, Xing G . N-acetyl-5-N,4-O-oxazolidinone-protected sialyl sulfoxide: an α-selective sialyl donor with Tf2O/(Tol)2SO in dichloromethane. Chem Asian J. 2012; 7(7):1524-8. DOI: 10.1002/asia.201200172. View

Noel A, Delpech B, Crich D . Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under Lewis acidic conditions. Org Lett. 2012; 14(16):4138-41. DOI: 10.1021/ol301779e. View

Crich D, Wu B . Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides. Org Lett. 2008; 10(18):4033-5. PMC: 2726932. DOI: 10.1021/ol801548k. View

Escoubet S, Gastaldi S, Vanthuyne N, Gil G, Siri D, Bertrand M . Thiyl radical mediated racemization of nonactivated aliphatic amines. J Org Chem. 2006; 71(19):7288-92. DOI: 10.1021/jo061033l. View

Olsson J, Eriksson L, Lahmann M, Oscarson S . Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors. J Org Chem. 2008; 73(18):7181-8. DOI: 10.1021/jo800971s. View

Noel A, Delpech B, Crich D . Stereoselective, electrophilic α-C-sialidation. Org Lett. 2012; 14(5):1342-5. DOI: 10.1021/ol300255q. View

Martichonok V, Whitesides G . Stereoselective alpha-Sialylation with Sialyl Xanthate and Phenylsulfenyl Triflate as a Promotor. J Org Chem. 1996; 61(5):1702-1706. DOI: 10.1021/jo951711w. View

Premathilake H, Demchenko A . Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis. Top Curr Chem. 2010; 301:189-221. PMC: 3150466. DOI: 10.1007/128_2010_106. View

Studer A . Tin-free radical chemistry using the persistent radical effect: alkoxyamine isomerization, addition reactions and polymerizations. Chem Soc Rev. 2004; 33(5):267-73. DOI: 10.1039/b307652k. View

10.

Peters K . Nature of dynamic processes associated with the S(N)1 reaction mechanism. Chem Rev. 2007; 107(3):859-73. DOI: 10.1021/cr068021k. View

11.

Denekamp C, Sandlers Y . Anomeric distinction and oxonium ion formation in acetylated glycosides. J Mass Spectrom. 2005; 40(6):765-71. DOI: 10.1002/jms.848. View

12.

Chu K, Ren C, Lu C, Hsu C, Sun T, Han J . Efficient and stereoselective synthesis of α(2→9) oligosialic acids: from monomers to dodecamers. Angew Chem Int Ed Engl. 2011; 50(40):9391-5. DOI: 10.1002/anie.201101794. View

13.

Yu R, LEDEEN R . Configuration of the ketosidic bond of sialic acid. J Biol Chem. 1969; 244(5):1306-13. View

14.

Litjens R, van den Bos L, Codee J, Overkleeft H, van der Marel G . The use of cyclic bifunctional protecting groups in oligosaccharide synthesis--an overview. Carbohydr Res. 2006; 342(3-4):419-29. DOI: 10.1016/j.carres.2006.09.002. View

15.

Okamoto R, Souma S, Kajihara Y . Efficient synthesis of MUC4 sialylglycopeptide through the new sialylation using 5-acetamido-neuraminamide donors. J Org Chem. 2008; 73(9):3460-6. DOI: 10.1021/jo702609p. View

16.

Gomez A . A survey of Ley's reactivity tuning in oligosaccharide synthesis. Top Curr Chem. 2011; 301:31-68. DOI: 10.1007/128_2010_112. View

17.

Akhlaq M, Schuchmann H, von Sonntag C . The reverse of the 'repair' reaction of thiols: H-abstraction at carbon by thiyl radicals. Int J Radiat Biol Relat Stud Phys Chem Med. 1987; 51(1):91-102. DOI: 10.1080/09553008714550531. View

18.

Cumpstey I . On a so-called "kinetic anomeric effect" in chemical glycosylation. Org Biomol Chem. 2012; 10(13):2503-8. DOI: 10.1039/c2ob06696c. View

19.

Crich D, Li W . alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialoside. J Org Chem. 2007; 72(20):7794-7. PMC: 3102260. DOI: 10.1021/jo7012912. View

20.

Yu G, Tyler D, Branchaud B . Thermal and photochemical epimerization/equilibration of carbohydrate cobaloximes. J Org Chem. 2001; 66(17):5687-91. DOI: 10.1021/jo005595v. View