Amide-to-ester substitution allows fine-tuning of the cyclopeptide conformational ensemble

Tommaso Cupido; Jan Spengler; Javier Ruiz-Rodriguez; Jaume Adan; Francesc Mitjans; Jaume Piulats; Fernando Albericio

doi:10.1002/anie.200907274

Amide-to-ester substitution allows fine-tuning of the cyclopeptide conformational ensemble

Tommaso Cupido
, Jan Spengler
, Javier Ruiz-Rodriguez
, Jaume Adan
, Francesc Mitjans
, Jaume Piulats
, Fernando Albericio

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

19 Scopus citations

Abstract

(Figure Presented) Without affecting the overall 3D structure, amide-to-ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RCD cyclopeptide cilengitide and its derivatives (see figure; RGD = Arg-GlyAsp). The appropriate substitution, which stabilized the receptor-complementary conformations, improved the biological activity of this integrin antagonist.

Original language	English
Pages (from-to)	2732-2737
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	15
DOIs	https://doi.org/10.1002/anie.200907274
State	Published - 1 Apr 2010
Externally published	Yes

Keywords

Bioorganic chemistry
Conformation analysis
Depsipeptides
Molecular dynamicsNMR spectroscopy

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10.1002/anie.200907274

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abstract = "(Figure Presented) Without affecting the overall 3D structure, amide-to-ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RCD cyclopeptide cilengitide and its derivatives (see figure; RGD = Arg-GlyAsp). The appropriate substitution, which stabilized the receptor-complementary conformations, improved the biological activity of this integrin antagonist.",

keywords = "Bioorganic chemistry, Conformation analysis, Depsipeptides, Molecular dynamicsNMR spectroscopy",

author = "Tommaso Cupido and Jan Spengler and Javier Ruiz-Rodriguez and Jaume Adan and Francesc Mitjans and Jaume Piulats and Fernando Albericio",

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T1 - Amide-to-ester substitution allows fine-tuning of the cyclopeptide conformational ensemble

AU - Cupido, Tommaso

AU - Spengler, Jan

AU - Ruiz-Rodriguez, Javier

AU - Adan, Jaume

AU - Mitjans, Francesc

AU - Piulats, Jaume

AU - Albericio, Fernando

PY - 2010/4/1

Y1 - 2010/4/1

N2 - (Figure Presented) Without affecting the overall 3D structure, amide-to-ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RCD cyclopeptide cilengitide and its derivatives (see figure; RGD = Arg-GlyAsp). The appropriate substitution, which stabilized the receptor-complementary conformations, improved the biological activity of this integrin antagonist.

AB - (Figure Presented) Without affecting the overall 3D structure, amide-to-ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RCD cyclopeptide cilengitide and its derivatives (see figure; RGD = Arg-GlyAsp). The appropriate substitution, which stabilized the receptor-complementary conformations, improved the biological activity of this integrin antagonist.

KW - Bioorganic chemistry

KW - Conformation analysis

KW - Depsipeptides

KW - Molecular dynamicsNMR spectroscopy

UR - https://www.scopus.com/pages/publications/77950473237

U2 - 10.1002/anie.200907274

DO - 10.1002/anie.200907274

M3 - Artículo

C2 - 20213784

AN - SCOPUS:77950473237

SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Amide-to-ester substitution allows fine-tuning of the cyclopeptide conformational ensemble

Abstract

Keywords

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