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

Dong Jun Lee; Renata Kowalczyk; Victoria J Muir; Phillip M Rendle; Margaret A Brimble

doi:10.1016/j.carres.2007.08.015

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

Carbohydr Res. 2007 Dec 10;342(17):2628-34. doi: 10.1016/j.carres.2007.08.015. Epub 2007 Aug 29.

Authors

Dong Jun Lee¹, Renata Kowalczyk, Victoria J Muir, Phillip M Rendle, Margaret A Brimble

Affiliation

¹ Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.

PMID: 17854783
DOI: 10.1016/j.carres.2007.08.015

Abstract

The synthesis of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-acetyl)-alpha-d-mannopyranosyl]-l-proline allyl ester and Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-alpha-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.

Publication types

Comparative Study

MeSH terms

Amino Acids / chemistry
Carbohydrate Conformation
Carbohydrates / chemistry
Chemistry / methods*
Esters / chemistry
Fluorenes / chemical synthesis*
Glycosylation
Lectins / chemistry
Magnetic Resonance Spectroscopy
Mannose / chemistry
Models, Chemical
Proline / analogs & derivatives*
Proline / chemical synthesis
Proline / chemistry*
Pyrans / chemistry*
Spectrophotometry / methods

Substances

Amino Acids
Carbohydrates
Esters
Fluorenes
Lectins
N2-fluorenylmethoxycarbonyl-4-hydroxyproline allyl ester
Pyrans
Proline
Mannose