A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline

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3 Citations (Scopus)

Abstract

A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.

Original languageEnglish (US)
Pages (from-to)4399-403
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number15
DOIs
StatePublished - Apr 21 2015

Fingerprint

Diketopiperazines
disulfides
Proline
routes
activation
preparation
synthesis
products
Cyclization
Biological Products
Disulfides
Libraries
Chemical activation
Derivatives
benzotriazole
cyclo(prolylprolyl)

Keywords

  • Animals
  • Biological Products
  • Cyclization
  • Diketopiperazines
  • Dipeptides
  • Ethylamines
  • Porifera
  • Proline
  • Stereoisomerism
  • Triazoles
  • Journal Article
  • Research Support, Non-U.S. Gov't

Cite this

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title = "A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline",
abstract = "A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.",
keywords = "Animals, Biological Products, Cyclization, Diketopiperazines, Dipeptides, Ethylamines, Porifera, Proline, Stereoisomerism, Triazoles, Journal Article, Research Support, Non-U.S. Gov't",
author = "Panda, {Siva S} and Iryna Lebedyeva",
year = "2015",
month = "4",
day = "21",
doi = "10.1039/c5ob00023h",
language = "English (US)",
volume = "13",
pages = "4399--403",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "15",

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TY - JOUR

T1 - A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline

AU - Panda, Siva S

AU - Lebedyeva, Iryna

PY - 2015/4/21

Y1 - 2015/4/21

N2 - A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.

AB - A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.

KW - Animals

KW - Biological Products

KW - Cyclization

KW - Diketopiperazines

KW - Dipeptides

KW - Ethylamines

KW - Porifera

KW - Proline

KW - Stereoisomerism

KW - Triazoles

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1039/c5ob00023h

DO - 10.1039/c5ob00023h

M3 - Article

C2 - 25762208

VL - 13

SP - 4399

EP - 4403

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 15

ER -