Automated synthesis of a protected N-linked glycoprotein core pentasaccharide

Daniel M Ratner; Erika R Swanson; Peter H Seeberger

doi:10.1021/ol035887t

Automated synthesis of a protected N-linked glycoprotein core pentasaccharide

Org Lett. 2003 Nov 27;5(24):4717-20. doi: 10.1021/ol035887t.

Authors

Daniel M Ratner¹, Erika R Swanson, Peter H Seeberger

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

PMID: 14627423
DOI: 10.1021/ol035887t

Abstract

[structure: see text] Described is the first automated solid-phase synthesis of the core N-linked pentasaccharide, common to all N-linked glycoproteins via stepwise assembly from mono- and disaccharide building blocks. The challenging beta-mannosidic linkage was incorporated by the inclusion of a disaccharide trichloroacetimidate. This automated synthesis provides rapid access to an oligosaccharide common to an entire class of glycoconjugates.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Acetamides
Automation
Carbohydrate Sequence
Chloroacetates*
Glycoproteins / chemical synthesis*
Glycoproteins / chemistry*
Molecular Sequence Data
Oligosaccharides / chemical synthesis*
Oligosaccharides / chemistry*
Trichloroacetic Acid / chemistry

Substances

Acetamides
Chloroacetates
Glycoproteins
Oligosaccharides
Trichloroacetic Acid
trichloroacetamide