Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support

Seiji Kamioka; Sayaka Shimazu; Takayuki Doi; Takashi Takahashi

doi:10.1021/cc800089m

Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support

Seiji Kamioka, Sayaka Shimazu, Takayuki Doi, Takashi Takahashi

PHA - Molecular Pharmaceutical Science

Tokyo Institute of Technology

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

13 Citations (Scopus)

Abstract

A combinatorial synthesis of 24-member RGD models was accomplished on polymer-support. Ortho-, meta-, and para-iodobenzylamines loaded on an aldehyde linker by reductive animation were coupled with RGD sequences and various ω-amino acids by a split-and-pool method. Palladium-catalyzed carbonylative macrolactamization of the polymer-supported cyclization precursors, followed by acid cleavage, provided conformationally restricted RGD model cyclic peptides.

Original language	English
Pages (from-to)	681-690
Number of pages	10
Journal	Journal of Combinatorial Chemistry
Volume	10
Issue number	5
DOIs	https://doi.org/10.1021/cc800089m
Publication status	Published - 2008 Sept

Access to Document

10.1021/cc800089m

Cite this

@article{60969c16ec614cc6b985fd1eea22ca7c,

title = "Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support",

abstract = "A combinatorial synthesis of 24-member RGD models was accomplished on polymer-support. Ortho-, meta-, and para-iodobenzylamines loaded on an aldehyde linker by reductive animation were coupled with RGD sequences and various ω-amino acids by a split-and-pool method. Palladium-catalyzed carbonylative macrolactamization of the polymer-supported cyclization precursors, followed by acid cleavage, provided conformationally restricted RGD model cyclic peptides.",

author = "Seiji Kamioka and Sayaka Shimazu and Takayuki Doi and Takashi Takahashi",

year = "2008",

month = sep,

doi = "10.1021/cc800089m",

language = "English",

volume = "10",

pages = "681--690",

journal = "Journal of Combinatorial Chemistry",

issn = "1520-4766",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support

AU - Kamioka, Seiji

AU - Shimazu, Sayaka

AU - Doi, Takayuki

AU - Takahashi, Takashi

PY - 2008/9

Y1 - 2008/9

N2 - A combinatorial synthesis of 24-member RGD models was accomplished on polymer-support. Ortho-, meta-, and para-iodobenzylamines loaded on an aldehyde linker by reductive animation were coupled with RGD sequences and various ω-amino acids by a split-and-pool method. Palladium-catalyzed carbonylative macrolactamization of the polymer-supported cyclization precursors, followed by acid cleavage, provided conformationally restricted RGD model cyclic peptides.

AB - A combinatorial synthesis of 24-member RGD models was accomplished on polymer-support. Ortho-, meta-, and para-iodobenzylamines loaded on an aldehyde linker by reductive animation were coupled with RGD sequences and various ω-amino acids by a split-and-pool method. Palladium-catalyzed carbonylative macrolactamization of the polymer-supported cyclization precursors, followed by acid cleavage, provided conformationally restricted RGD model cyclic peptides.

UR - http://www.scopus.com/inward/record.url?scp=53049095529&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=53049095529&partnerID=8YFLogxK

U2 - 10.1021/cc800089m

DO - 10.1021/cc800089m

M3 - Article

C2 - 18683986

AN - SCOPUS:53049095529

SN - 1520-4766

VL - 10

SP - 681

EP - 690

JO - Journal of Combinatorial Chemistry

JF - Journal of Combinatorial Chemistry

IS - 5

ER -

Combinatorial synthesis of RGD model cyclic peptides utilizing a palladium-catalyzed carbonylative macrolactamization on a polymer support

Abstract

Access to Document

Other files and links

Fingerprint

Cite this