Regio- and stereoselective α-alkylation of N-terminal amino acid residue of peptides using a pyridoxal model compound with a chiral ansa-structure

Regio- and stereoselective α-alkylation of N-terminal amino acid residue of peptides was achieved by Li +-mediated alkylation of aldimines prepared from the peptides and a pyridoxal model compound having a chiral ansa-structure and an ethoxyethoxy group at C-3. The stereochemistry and stereoselectiv...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2001-07, Vol.57 (27), p.5773-5780
Main Authors: Miyashita, Kazuyuki, Iwaki, Hiroshi, Tai, Kuninori, Murafuji, Hidenobu, Sasaki, Naoko, Imanishi, Takeshi
Format: Article
Language:English
Subjects:
alkylation
cyclophanes
peptide
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Regio- and stereoselective α-alkylation of N-terminal amino acid residue of peptides was achieved by Li +-mediated alkylation of aldimines prepared from the peptides and a pyridoxal model compound having a chiral ansa-structure and an ethoxyethoxy group at C-3. The stereochemistry and stereoselectivity of the reaction were found to be influenced predominantly by the chirality of the model compound and Li +, but little by the stereochemistry of the original peptides. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00512-9