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

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

18 Citas (Scopus)

Resumen

(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.

Idioma original	Inglés
Páginas (desde-hasta)	2732-2737
Número de páginas	6
Publicación	Angewandte Chemie - International Edition
Volumen	49
N.º	15
DOI	https://doi.org/10.1002/anie.200907274
Estado	Publicada - 1 abr. 2010
Publicado de forma externa	Sí

Acceder al documento

10.1002/anie.200907274

Otros archivos y enlaces

Enlace a la publicación en Scopus

Citar esto

@article{0a60f590fa9848f78a2f31bcad0590b1,

title = "Amide-to-ester substitution allows fine-tuning of the cyclopeptide conformational ensemble",

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",

year = "2010",

month = apr,

day = "1",

doi = "10.1002/anie.200907274",

language = "Ingl{\'e}s",

volume = "49",

pages = "2732--2737",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "15",

}

TY - JOUR

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

VL - 49

SP - 2732

EP - 2737

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

Resumen

Acceder al documento

Otros archivos y enlaces

Huella

Citar esto