Piperazine-2,3,5-triones in the synthesis of constrained peptides

Patrick D. Bailey; Andrew N. Boa; S. Richard Baker; Joanne Clayson; Ernest J. Murray; Georgina M. Rosair

doi:10.1016/S0040-4039(99)01602-0

Piperazine-2,3,5-triones in the synthesis of constrained peptides

Patrick D. Bailey, Andrew N. Boa, S. Richard Baker, Joanne Clayson, Ernest J. Murray, Georgina M. Rosair

School of Engineering & Physical Sciences

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

5 Citations (Scopus)

Abstract

Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N⁴, bis-alkylated at N⁴ and C⁶, or tris-alkylated at N⁴, N¹, and C⁶ under mild basic conditions; this provides access to i) a,a-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(a)-N bond formation; iii) DKP analogues.

Original language	English
Pages (from-to)	7557-7560
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	42
DOIs	https://doi.org/10.1016/S0040-4039(99)01602-0
Publication status	Published - 15 Oct 1999

Keywords

Amino acids and derivatives
Peptide analogues/mimetics
Piperazines/piperazinones

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10.1016/S0040-4039(99)01602-0

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title = "Piperazine-2,3,5-triones in the synthesis of constrained peptides",

abstract = "Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N4, bis-alkylated at N4 and C6, or tris-alkylated at N4, N1, and C6 under mild basic conditions; this provides access to i) a,a-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(a)-N bond formation; iii) DKP analogues.",

keywords = "Amino acids and derivatives, Peptide analogues/mimetics, Piperazines/piperazinones",

author = "Bailey, \{Patrick D.\} and Boa, \{Andrew N.\} and Baker, \{S. Richard\} and Joanne Clayson and Murray, \{Ernest J.\} and Rosair, \{Georgina M.\}",

year = "1999",

month = oct,

day = "15",

doi = "10.1016/S0040-4039(99)01602-0",

language = "English",

volume = "40",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Piperazine-2,3,5-triones in the synthesis of constrained peptides

AU - Bailey, Patrick D.

AU - Boa, Andrew N.

AU - Baker, S. Richard

AU - Clayson, Joanne

AU - Murray, Ernest J.

AU - Rosair, Georgina M.

PY - 1999/10/15

Y1 - 1999/10/15

N2 - Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N4, bis-alkylated at N4 and C6, or tris-alkylated at N4, N1, and C6 under mild basic conditions; this provides access to i) a,a-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(a)-N bond formation; iii) DKP analogues.

AB - Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N4, bis-alkylated at N4 and C6, or tris-alkylated at N4, N1, and C6 under mild basic conditions; this provides access to i) a,a-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(a)-N bond formation; iii) DKP analogues.

KW - Amino acids and derivatives

KW - Peptide analogues/mimetics

KW - Piperazines/piperazinones

UR - https://www.scopus.com/pages/publications/0033570268

U2 - 10.1016/S0040-4039(99)01602-0

DO - 10.1016/S0040-4039(99)01602-0

M3 - Article

SN - 0040-4039

VL - 40

SP - 7557

EP - 7560

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Piperazine-2,3,5-triones in the synthesis of constrained peptides

Abstract

Keywords

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