Cyclization of linear tetrapeptides containing N-nethylated amino acids by using 1-propanephosphonic acid anhydride

Shengping Zhang, Luis M. De Leon Rodriguez, Ernest Lacey, Andrew M. Piggott, Ivanhoe K. H. Leung, Margaret A. Brimble

Research output: Contribution to journalArticle

Abstract

The cyclization of the linear tetrapeptides sequence H-NMePhe-Xaa1-NMePhe-Xaa2-OH (for which Xaa1 = Xaa2 = Ile, Val, or Leu; Xaa1 = Val; Xaa2 = Ile or Leu) by using 1-propanephosphonic acid anhydride was explored. An unanticipated finding is the cyclization towards cyclotetrapeptide conformers (kinetic products) that were highly prone to hydrolysis and that slowly interconvert into the more stable trans,cis,trans,cis (tctc) conformers (thermodynamic products).

LanguageEnglish
Pages149-158
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number1
DOIs
StatePublished - 2017

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Anhydrides
Cyclization
anhydrides
amino acids
Amino Acids
acids
Acids
products
hydrolysis
Hydrolysis
Thermodynamics
thermodynamics
Kinetics
kinetics

Cite this

Zhang, Shengping ; De Leon Rodriguez, Luis M. ; Lacey, Ernest ; Piggott, Andrew M. ; Leung, Ivanhoe K. H. ; Brimble, Margaret A./ Cyclization of linear tetrapeptides containing N-nethylated amino acids by using 1-propanephosphonic acid anhydride. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 1. pp. 149-158
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keywords = "Cyclization, Tetrapeptides, Conformation analysis, Natural products, Biological activity",
author = "Shengping Zhang and {De Leon Rodriguez}, {Luis M.} and Ernest Lacey and Piggott, {Andrew M.} and Leung, {Ivanhoe K. H.} and Brimble, {Margaret A.}",
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Cyclization of linear tetrapeptides containing N-nethylated amino acids by using 1-propanephosphonic acid anhydride. / Zhang, Shengping; De Leon Rodriguez, Luis M.; Lacey, Ernest; Piggott, Andrew M.; Leung, Ivanhoe K. H.; Brimble, Margaret A.

In: European Journal of Organic Chemistry, Vol. 2017, No. 1, 2017, p. 149-158.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Cyclization of linear tetrapeptides containing N-nethylated amino acids by using 1-propanephosphonic acid anhydride

AU - Zhang,Shengping

AU - De Leon Rodriguez,Luis M.

AU - Lacey,Ernest

AU - Piggott,Andrew M.

AU - Leung,Ivanhoe K. H.

AU - Brimble,Margaret A.

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AB - The cyclization of the linear tetrapeptides sequence H-NMePhe-Xaa1-NMePhe-Xaa2-OH (for which Xaa1 = Xaa2 = Ile, Val, or Leu; Xaa1 = Val; Xaa2 = Ile or Leu) by using 1-propanephosphonic acid anhydride was explored. An unanticipated finding is the cyclization towards cyclotetrapeptide conformers (kinetic products) that were highly prone to hydrolysis and that slowly interconvert into the more stable trans,cis,trans,cis (tctc) conformers (thermodynamic products).

KW - Cyclization

KW - Tetrapeptides

KW - Conformation analysis

KW - Natural products

KW - Biological activity

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