First total synthesis of a GPI-anchored peptide

Jie Xue; Ning Shao; Zhongwu Guo

doi:10.1021/jo034213t

First total synthesis of a GPI-anchored peptide

J Org Chem. 2003 May 16;68(10):4020-9. doi: 10.1021/jo034213t.

Authors

Jie Xue¹, Ning Shao, Zhongwu Guo

Affiliation

¹ Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106-7078, USA.

PMID: 12737586
DOI: 10.1021/jo034213t

Abstract

A GPI-anchored dipeptide of sperm CD52 antigen was prepared through a convergent synthesis. First, the dipeptide with its C-terminus free and the GPI with its nonreducing end phosphoethanolamine bearing a free amino group were synthesized separately. Then, the two building blocks were coupled with use of EDC/HOBt as the condensation reagent. Finally, the GPI-anchored peptide was deprotected to give the target molecule 1.

Publication types

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

MeSH terms

Antigens, CD / chemistry*
Antigens, Neoplasm / chemistry*
CD52 Antigen
Catalysis
Combinatorial Chemistry Techniques*
Glycoproteins / chemistry*
Glycosylphosphatidylinositols / chemical synthesis*
Glycosylphosphatidylinositols / chemistry
Humans
Indicators and Reagents
Male
Membrane Glycoproteins / chemical synthesis*
Membrane Glycoproteins / chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Spermatozoa / chemistry*
Structure-Activity Relationship

Substances

Antigens, CD
Antigens, Neoplasm
CD52 Antigen
CD52 protein, human
Glycoproteins
Glycosylphosphatidylinositols
Indicators and Reagents
Membrane Glycoproteins