Triproline analogues of Pro-Leu-Gly-NH2 with Pro/Leu and Pro/Phe chimeric amino acids in position 2

Authors
Evans, MC Johnson, RL
Citation
Mc. Evans et Rl. Johnson, Triproline analogues of Pro-Leu-Gly-NH2 with Pro/Leu and Pro/Phe chimeric amino acids in position 2, TETRAHEDRON, 56(50), 2000, pp. 9801-9808
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
50
Year of publication
2000
Pages
9801 - 9808
Database
ISI
SICI code
0040-4020(200012)56:50<9801:TAOPWP>2.0.ZU;2-1
Abstract
Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (S-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefi n. These chimeric amino acids were incorporated into the triprolyl analogue s of Pro-Leu-Gly-NH2: Pro-cia 3-i-Pr-Pro-Pro-NH2 (3), Pro-trans-3-i-Pr-Pro- Pro-NH2 (4), Pro-cis-3-Ph-Pro-Pro-NH2 (5), Pro-trans-3-Ph-Pro-Pro-NH2 (6). (C) 2000 Elsevier Science Ltd. All rights reserved.