Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker

Peter Vertesaljai; Iryna O. Lebedyeva; Alexander A. Oliferenko; Xin Qi; Junjie Fu; David A. Ostrov; Abdullah M. Asiri; C. Dennis Hall; Alan Katritzky

doi:10.1016/j.tetlet.2015.09.063

Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker

Peter Vertesaljai
, Iryna O. Lebedyeva
, Alexander A. Oliferenko
, Xin Qi
, Junjie Fu
, David A. Ostrov
, Abdullah M. Asiri
, C. Dennis Hall
, Alan Katritzky

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

2 Scopus citations

Abstract

In this work the five-step assembly of a peptidomimetic structurally resembling Prolyl-Prolyl-Proline tripeptide is reported. Proline units are mimicked by two pyrazolidine rings connected to trans-1,2-cyclopentanedicarboxylic acid. The Pro-Pro-Pro mimetic resembles a tri-l-proline unit but with increased lipophilicity and structural constraints imposed by the linker.

Original language	English (US)
Pages (from-to)	6653-6655
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.063
State	Published - Jul 13 2015

Keywords

Coupling
Heterocycles
Peptide
Peptidomimetic
Proline

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.09.063

Cite this

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title = "Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker",

abstract = "In this work the five-step assembly of a peptidomimetic structurally resembling Prolyl-Prolyl-Proline tripeptide is reported. Proline units are mimicked by two pyrazolidine rings connected to trans-1,2-cyclopentanedicarboxylic acid. The Pro-Pro-Pro mimetic resembles a tri-l-proline unit but with increased lipophilicity and structural constraints imposed by the linker.",

keywords = "Coupling, Heterocycles, Peptide, Peptidomimetic, Proline",

author = "Peter Vertesaljai and Lebedyeva, \{Iryna O.\} and Oliferenko, \{Alexander A.\} and Xin Qi and Junjie Fu and Ostrov, \{David A.\} and Asiri, \{Abdullah M.\} and \{Dennis Hall\}, C. and Alan Katritzky",

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doi = "10.1016/j.tetlet.2015.09.063",

language = "English (US)",

volume = "56",

pages = "6653--6655",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "48",

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TY - JOUR

T1 - Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker

AU - Vertesaljai, Peter

AU - Lebedyeva, Iryna O.

AU - Oliferenko, Alexander A.

AU - Qi, Xin

AU - Fu, Junjie

AU - Ostrov, David A.

AU - Asiri, Abdullah M.

AU - Dennis Hall, C.

AU - Katritzky, Alan

PY - 2015/7/13

Y1 - 2015/7/13

N2 - In this work the five-step assembly of a peptidomimetic structurally resembling Prolyl-Prolyl-Proline tripeptide is reported. Proline units are mimicked by two pyrazolidine rings connected to trans-1,2-cyclopentanedicarboxylic acid. The Pro-Pro-Pro mimetic resembles a tri-l-proline unit but with increased lipophilicity and structural constraints imposed by the linker.

AB - In this work the five-step assembly of a peptidomimetic structurally resembling Prolyl-Prolyl-Proline tripeptide is reported. Proline units are mimicked by two pyrazolidine rings connected to trans-1,2-cyclopentanedicarboxylic acid. The Pro-Pro-Pro mimetic resembles a tri-l-proline unit but with increased lipophilicity and structural constraints imposed by the linker.

KW - Coupling

KW - Heterocycles

KW - Peptide

KW - Peptidomimetic

KW - Proline

UR - https://www.scopus.com/pages/publications/84955214233

UR - https://www.scopus.com/pages/publications/84955214233#tab=citedBy

U2 - 10.1016/j.tetlet.2015.09.063

DO - 10.1016/j.tetlet.2015.09.063

M3 - Article

AN - SCOPUS:84955214233

SN - 0040-4039

VL - 56

SP - 6653

EP - 6655

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker

Abstract

Keywords

ASJC Scopus subject areas

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