Premium
Preparation of Sugar Amino Acids by Claisen‐Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues
Author(s) -
Montero Ana,
Mann Enrique,
Herradón Bernardo
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400166
Subject(s) - chemistry , claisen rearrangement , stereoselectivity , sugar , azide , stereochemistry , amino acid , carboxylic acid , amino sugar , organic chemistry , biochemistry , catalysis
We have developed a convenient route for the synthesis of an unsaturated branched sugar bearing a carboxylic acid and an amino group (masked as an azide group) by employing a totally stereoselective Claisen−Johnson rearrangement as the key step. Several Met‐ and Leu‐enkephalin analogues with different substitution patterns at the N ‐ and C ‐termini were prepared by incorporating this sugar amino acid (SAA) as a substitute for the central Gly−Gly fragment of the parent pentapeptides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)