Solid phase synthesis of peptides containing backbone-fluorinated amino acids

被引：26

作者：

Hunter, Luke ^{[1
,2
]}

Butler, Sharon ^{[3
]}

Ludbrook, Steven B. ^{[3
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

[3] GlaxoSmithKline Res & Dev Ltd, Dept Screening & Compound Profiling, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 44期

关键词：

DESIGN; NMR; ALPHA(V)BETA(3); 3(14)-HELIX; STABILITY; INTEGRINS; PROTEINS; RECEPTOR;

D O I：

10.1039/c2ob26596f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Backbone-fluorinated amino acids exhibit unique conformational behaviour, and have potential utility as components of bioactive shape-controlled peptides. However, methods for the elaboration of backbone-fluorinated amino acids have thus far been limited to solution phase peptide coupling reactions. In this paper, protocols are developed that allow the successful manipulation of backbone-fluorinated amino acids using Fmoc-strategy solid phase peptide synthesis. To exemplify this strategy, several fluorinated RGD peptide analogues were synthesised in moderate to good overall yields.

引用

页码：8911 / 8918

页数：8

共 50 条

[1] Ribosomal Synthesis of Backbone-Macrocyclic Peptides Containing γ-Amino Acids
Ohshiro, Yukinori
Nakajima, Eiji
Goto, Yuki
Fuse, Shinichiro
Takahashi, Takashi
Doi, Takayuki
Suga, Hiroaki
CHEMBIOCHEM, 2011, 12 (08) : 1183 - 1187
[2] Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines
Małgorzata Koprowska-Ratajska
Alicja Kluczyk
Piotr Stefanowicz
Hubert Bartosz-Bechowski
Zbigniew Szewczuk
Amino Acids, 2009, 36
[3] Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines
Koprowska-Ratajska, Malgorzata
Kluczyk, Alicja
Stefanowicz, Piotr
Bartosz-Bechowski, Hubert
Szewczuk, Zbigniew
AMINO ACIDS, 2009, 36 (02) : 309 - 315
[4] Solid-phase synthesis of peptides containing α,β-didehydroamino acids
Royo, M
Jiménez, JC
López-Macià, A
Giralt, E
Albericio, F
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (01) : 45 - 48
[5] Backbone-Fluorinated 1,2,3-Triazole-Containing Dipeptide Surrogates
Engel-Andreasen, Jens
Wellhofer, Isabelle
Wich, Kathrine
Olsen, Christian A.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21): : 11613 - 11619
[6] Recent advances in the synthesis of fluorinated amino acids and peptides
Zhou, Minqi
Feng, Zhang
Zhang, Xingang
CHEMICAL COMMUNICATIONS, 2023, 59 (11) : 1434 - 1448
[7] The Barton radical decarboxylation on solid phase. A versatile synthesis of peptides containing modified amino acids
Attardi, ME
Taddei, M
TETRAHEDRON LETTERS, 2001, 42 (20) : 3519 - 3522
[8] Solid phase synthesis of α-amino squaric acid-containing peptides
Maeda, Kentaro
Kiniwa, Yu-ichi
Ohfune, Yasufumi
Ishiguro, Shinichi
Suzuki, Koichi
Murata, Kazuya
Matsuda, Hideaki
Shinada, Tetsuro
RSC ADVANCES, 2014, 4 (92) : 50639 - 50643
[9] Solid-phase synthesis of peptides containing bulky dehydroamino acids
Jiang, Jintao
Luo, Shi
Castle, Steven L.
TETRAHEDRON LETTERS, 2015, 56 (23) : 3311 - 3313
[10] Photoinduced radical hydroperfluoroalkylation and the synthesis of fluorinated amino acids and peptides
Yajima, Tomoko
Yamaguchi, Kanako
Hirokane, Rie
Nogami, Emiko
JOURNAL OF FLUORINE CHEMISTRY, 2013, 150 : 1 - 7

← 1 2 3 4 5 →