A comparative study of different glycosylation methods for the synthesis of D-mannopyranosides of Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester

Lee, Danny; Kowalczyk, Renata; Muir, Victoria; Rendle, PM; Brimble, Margaret

dc.contributor.author	Lee, Danny	en
dc.contributor.author	Kowalczyk, Renata	en
dc.contributor.author	Muir, Victoria	en
dc.contributor.author	Rendle, PM	en
dc.contributor.author	Brimble, Margaret	en
dc.date.accessioned	2011-09-18T22:36:09Z	en
dc.date.issued	2007	en
dc.identifier.citation	Carbohydrate Research 342(17):2628-2634 2007	en
dc.identifier.issn	0008-6215	en
dc.identifier.uri	http://hdl.handle.net/2292/7998	en
dc.description.abstract	The synthesis of Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-acetyl)-α-d-mannopyranosyl]-l-proline allyl ester and Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-α-d-mannopyranosyl]-l-proline allyl ester is described. Glycosylation using Königs–Knorr conditions with a benzoyl protected glycosyl donor provided the optimum method. Removal of the allyl ester gave two mannosylated building blocks suitable for solid phase glycopeptide synthesis.	en
dc.language	EN	en
dc.publisher	Elsevier Ltd.	en
dc.relation.ispartofseries	Carbohydrate Research	en
dc.rights	Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0008-6215/	en
dc.rights.uri	https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm	en
dc.subject	sugar amino acids	en
dc.subject	trans-4-hydroxy-proline	en
dc.subject	mannose	en
dc.subject	O-glycosylation	en
dc.subject	vaccines and C-lectins	en
dc.subject	SOLID-PHASE SYNTHESIS	en
dc.subject	BUILDING-BLOCKS	en
dc.subject	MORPHICEPTIN ANALOGS	en
dc.subject	O-GLYCOSYL	en
dc.subject	HYDROXYPROLINE	en
dc.subject	DERIVATIVES	en
dc.subject	PEPTIDE	en
dc.subject	ALPHA	en
dc.subject	THIOGLYCOSIDES	en
dc.subject	GLYCOPEPTIDES	en
dc.title	A comparative study of different glycosylation methods for the synthesis of D-mannopyranosides of Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester	en
dc.type	Journal Article	en
dc.identifier.doi	10.1016/j.carres.2007.08.015	en
pubs.issue	17	en
pubs.begin-page	2628	en
pubs.volume	342	en
dc.rights.holder	Copyright: 2007 Elsevier Ltd.	en
dc.identifier.pmid	17854783	en
pubs.end-page	2634	en
dc.rights.accessrights	http://purl.org/eprint/accessRights/RestrictedAccess	en
pubs.subtype	Article	en
pubs.elements-id	74025	en
pubs.org-id	Science	en
pubs.org-id	Chemistry	en
pubs.org-id	Science Research	en
pubs.org-id	Maurice Wilkins Centre (2010-2014)	en
pubs.record-created-at-source-date	2010-09-01	en
pubs.dimensions-id	17854783	en