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

Margaret C. Evans; Rodney L. Johnson

doi:10.1016/S0040-4020(00)00887-5

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

Margaret C. Evans, Rodney L. Johnson

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (3-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefin. These chimeric amino acids were incorporated into the triprolyl analogues of Pro-Leu-Gly-NH₂: Pro-cis-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.

Original language	English (US)
Pages (from-to)	9801-9808
Number of pages	8
Journal	Tetrahedron
Volume	56
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4020(00)00887-5
State	Published - Dec 8 2000

Bibliographical note

Funding Information:
This work was supported in part by an NIH grant (NS20036) to R. L. J. The authors thank Tom Crick for mass spectral analysis.

Keywords

Chimeric amino acids
Proline-leucine
Triproline analogue

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

abstract = "Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (3-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefin. These chimeric amino acids were incorporated into the triprolyl analogues of Pro-Leu-Gly-NH2: Pro-cis-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.",

keywords = "Chimeric amino acids, Proline-leucine, Triproline analogue",

author = "Evans, {Margaret C.} and Johnson, {Rodney L.}",

note = "Funding Information: This work was supported in part by an NIH grant (NS20036) to R. L. J. The authors thank Tom Crick for mass spectral analysis. ",

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AU - Evans, Margaret C.

AU - Johnson, Rodney L.

N1 - Funding Information: This work was supported in part by an NIH grant (NS20036) to R. L. J. The authors thank Tom Crick for mass spectral analysis.

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Y1 - 2000/12/8

N2 - Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (3-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefin. These chimeric amino acids were incorporated into the triprolyl analogues of Pro-Leu-Gly-NH2: Pro-cis-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.

AB - Synthesis of the cis- and trans-isomers of the proline-leucine (3-i-Pr-Pro) and proline-phenylalanine (3-Ph-Pro) chimeric amino acids was accomplished by intramolecular reductive-cycloalkylation of the appropriate azido-olefin. These chimeric amino acids were incorporated into the triprolyl analogues of Pro-Leu-Gly-NH2: Pro-cis-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.

KW - Chimeric amino acids

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