Preparation of Sugar Amino Acids by Claisen‐Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues | Zendy

Montero Ana | Zendy; Mann Enrique | Zendy; Herradón Bernardo | Zendy

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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)

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