ASYMMETRIC-SYNTHESIS OF BOC-N-METHYL-P-BENZOYL-PHENYLALANINE - PREPARATION OF A PHOTOREACTIVE ANTAGONIST OF SUBSTANCE-P

Authors
KAROYAN P SAGAN S CLODIC G LAVIELLE S CHASSAING G
Citation
P. Karoyan et al., ASYMMETRIC-SYNTHESIS OF BOC-N-METHYL-P-BENZOYL-PHENYLALANINE - PREPARATION OF A PHOTOREACTIVE ANTAGONIST OF SUBSTANCE-P, Bioorganic & medicinal chemistry letters, 8(11), 1998, pp. 1369-1374
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
8
Issue
11
Year of publication
1998
Pages
1369 - 1374
Database
ISI
SICI code
0960-894X(1998)8:11<1369:AOB-P>2.0.ZU;2-R
Abstract
The asymmetric synthesis of (S)-Boc-N-methyl-p-benzoyl-phenylalanine w as performed by alkylation of sultam Boc-sarcosinate. The levorotatory sultam led to (S)-Boc-N-methyl amino acids with high optical purity. This photoreactive amino acid was incorporated into the sequence of a Substance P peptide antagonist. Comparison of the affinity and antagon istic properties of Biotinyl-apa-[D-Pro(9), MePhe(pBz)(10), Trp(11)]SP for human tachykinin NK-1 receptor demonstrated that this photoreacti ve antagonist should be a suitable tool for photolabelling studies, (C ) 1998 Elsevier Science Ltd. All rights reserved.