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

doi:10.1002/ejoc.201601016

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^*

^*Corresponding author for this work

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

14 Citations (Scopus)

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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).

Original language	English
Pages (from-to)	149-158
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201601016
Publication status	Published - 3 Jan 2017

Bibliographical note

Copyright the Publisher 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

Cyclization
Tetrapeptides
Conformation analysis
Natural products
Biological activity

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10.1002/ejoc.201601016

Accepted author manuscriptAccepted author manuscript, 3.27 MB

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

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).",

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.}",

note = "Copyright the Publisher 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher. ",

year = "2017",

month = jan,

day = "3",

doi = "10.1002/ejoc.201601016",

language = "English",

volume = "2017",

pages = "149--158",

journal = "European Journal of Organic Chemistry",

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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.

N1 - Copyright the Publisher 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

PY - 2017/1/3

Y1 - 2017/1/3

N2 - 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).

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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UR - http://purl.org/au-research/grants/arc/FT130100142

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DO - 10.1002/ejoc.201601016

M3 - Article

AN - SCOPUS:85006381001

VL - 2017

SP - 149

EP - 158

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 1

ER -

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

Abstract

Bibliographical note

Keywords

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