A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

Dimitris Georgiadis; Magdalini Matziari; Stamatia Vassiliou; Vincent Dive; Athanasios Yiotakis

doi:10.1016/S0040-4020(99)00910-2

A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

Dimitris Georgiadis^*
, Magdalini Matziari
, Stamatia Vassiliou
, Vincent Dive
, Athanasios Yiotakis

^*Corresponding author for this work

National and Kapodistrian University of Athens
CEA/Saclay

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

40 Citations (Scopus)

Abstract

Many attempts to synthesize AspΨ(PO₂CH₂)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected PheΨ(PO₂CH₂)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.

Original language	English
Pages (from-to)	14635-14648
Number of pages	14
Journal	Tetrahedron
Volume	55
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4020(99)00910-2
Publication status	Published - 17 Dec 1999
Externally published	Yes

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10.1016/S0040-4020(99)00910-2

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title = "A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon",

abstract = "Many attempts to synthesize AspΨ(PO2CH2)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected PheΨ(PO2CH2)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.",

author = "Dimitris Georgiadis and Magdalini Matziari and Stamatia Vassiliou and Vincent Dive and Athanasios Yiotakis",

note = "Funding Information: Acknowledgments:T his work was supportedb y funds from the University of",

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doi = "10.1016/S0040-4020(99)00910-2",

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T1 - A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

AU - Georgiadis, Dimitris

AU - Matziari, Magdalini

AU - Vassiliou, Stamatia

AU - Dive, Vincent

AU - Yiotakis, Athanasios

N1 - Funding Information: Acknowledgments:T his work was supportedb y funds from the University of

PY - 1999/12/17

Y1 - 1999/12/17

N2 - Many attempts to synthesize AspΨ(PO2CH2)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected PheΨ(PO2CH2)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.

AB - Many attempts to synthesize AspΨ(PO2CH2)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected PheΨ(PO2CH2)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.

UR - https://www.scopus.com/pages/publications/0033579657

U2 - 10.1016/S0040-4020(99)00910-2

DO - 10.1016/S0040-4020(99)00910-2

M3 - Article

AN - SCOPUS:0033579657

SN - 0040-4020

VL - 55

SP - 14635

EP - 14648

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -

A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

Abstract

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