New principles for glycoside-bond formation
- PMID: 19173361
- DOI: 10.1002/anie.200802036
New principles for glycoside-bond formation
Abstract
Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.
Similar articles
-
2-nitroglycals as powerful glycosyl donors: application in the synthesis of biologically important molecules.Acc Chem Res. 2008 Aug;41(8):1059-73. doi: 10.1021/ar7002495. Epub 2008 Jul 4. Acc Chem Res. 2008. PMID: 18598060 Review.
-
Large-scale enzymatic synthesis of oligosaccharides.Curr Opin Drug Discov Devel. 2000 Nov;3(6):756-63. Curr Opin Drug Discov Devel. 2000. PMID: 19649904
-
Sweet antibiotics - the role of glycosidic residues in antibiotic and antitumor activity and their randomization.FEMS Microbiol Rev. 2008 Aug;32(5):858-89. doi: 10.1111/j.1574-6976.2008.00124.x. Epub 2008 Jul 18. FEMS Microbiol Rev. 2008. PMID: 18647177 Review.
-
Advances in glycoside and oligosaccharide synthesis.Chem Soc Rev. 2023 Nov 13;52(22):7773-7801. doi: 10.1039/d3cs00321c. Chem Soc Rev. 2023. PMID: 37830906 Review.
-
Marine glycosyl hydrolases in the hydrolysis and synthesis of oligosaccharides.Biotechnol J. 2006 May;1(5):511-30. doi: 10.1002/biot.200500036. Biotechnol J. 2006. PMID: 16892287 Review.
Cited by
-
Chemical O-Glycosylations: An Overview.ChemistryOpen. 2016 Aug 17;5(5):401-433. doi: 10.1002/open.201600043. eCollection 2016 Oct. ChemistryOpen. 2016. PMID: 27777833 Free PMC article. Review.
-
Novel galactosyl donor with 2-naphthylmethyl (NAP) as the non participating group at C-2 position: Efficient synthesis of alpha-galactosyl ceramide.Tetrahedron Lett. 2010 Aug 18;51(33):4411-4414. doi: 10.1016/j.tetlet.2010.06.071. Tetrahedron Lett. 2010. PMID: 20730042 Free PMC article.
-
Benzyne arylation of oxathiane glycosyl donors.Beilstein J Org Chem. 2010 Feb 22;6:19. doi: 10.3762/bjoc.6.19. Beilstein J Org Chem. 2010. PMID: 20485601 Free PMC article.
-
Recyclable fluorous-tag assisted two-directional oligosaccharide synthesis enabled by interrupted Pummerer reaction mediated glycosylation.Chem Sci. 2022 Jun 22;13(30):8759-8765. doi: 10.1039/d2sc01700h. eCollection 2022 Aug 4. Chem Sci. 2022. PMID: 35975149 Free PMC article.
-
Efficient routes toward the synthesis of the D-rhamno-trisaccharide related to the A-band polysaccharide of Pseudomonas aeruginosa.Beilstein J Org Chem. 2014 Jul 1;10:1488-94. doi: 10.3762/bjoc.10.153. eCollection 2014. Beilstein J Org Chem. 2014. PMID: 25161705 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous