Article

Protecting group variations of delta-mercaptolysine useful in chemical ubiquitylation.

Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel.
Biopolymers (impact factor: 2.87). 01/2010; 94(4):504-10. DOI:10.1002/bip.21384 pp.504-10
Source: PubMed

ABSTRACT The high efficiency and chemoselectivity of peptide ubiquitylation that is achieved using the delta-mercaptolysine prompted us to expand the scope of this residue in various ligation schemes. In this report, we demonstrate the synthesis of five analogues of this important amino acid bearing a variety of protecting groups, which is essential in sequential peptide ligation and ubiquitylation. The key-step in the synthesis is the nucleophilic 1,4-addition of a variety of thiols on a nitro olefin scaffold.

0 0
 · 
0 Bookmarks
 · 
19 Views
Data provided are for informational purposes only. Although carefully collected, accuracy cannot be guaranteed. The impact factor represents a rough estimation of the journal's impact factor and does not reflect the actual current impact factor. Publisher conditions are provided by RoMEO. Differing provisions from the publisher's actual policy or licence agreement may be applicable.

Keywords

amino acid bearing
 
essential
 
nitro olefin scaffold
 
nucleophilic 1,4-addition
 
peptide ubiquitylation
 
sequential peptide ligation
 
ubiquitylation
 
various ligation schemes
 

Mahmood Haj-Yahya