A universal strategy for preparing protected C-terminal peptides on the solid phase through an intramolecular click chemistry-based handle

被引：10

作者：

Gongora-Benitez, Miriam ^{[2
]}

Cristau, Michele ^{[1
]}

Giraud, Matthieu ^{[1
]}

Tulla-Puche, Judit ^{[2
,3
]}

Albericio, Fernando ^{[2
,3
,4
]}

机构：

[1] Lonza Ltd, CH-3930 Visp, Switzerland

[2] Inst Res Biomed, Barcelona 08028, Spain

[3] PCB, Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona 08028, Spain

[4] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 17期

关键词：

DIKETOPIPERAZINE FORMATION;

D O I：

10.1039/c2cc17222d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new universal strategy exploits DKP formation in a dipeptide moiety whose C-terminal residue is blocked by a leaving group. It enables both synthesis of C-terminal protected peptides that are useful for convergent synthesis of large peptides and use of a C-terminal permanent protecting group that can be cleaved by catalytic hydrogenation to release the peptide.

引用

页码：2313 / 2315

页数：3

共 50 条

[21] Fmoc solid-phase synthesis of C-terminal modified peptides by formation of a backbone cyclic urethane moiety
Elashal, Hader E.
Cohen, Ryan D.
Raj, Monika
CHEMICAL COMMUNICATIONS, 2016, 52 (62) : 9699 - 9702
[22] Silyl-Based Alkyne-Modifying Linker for the Preparation of C-Terminal Acetylene-Derivatized Protected Peptides
Strack, Martin
Langklotz, Sina
Bandow, Julia E.
Metzler-Nolte, Nils
Albada, H. Bauke
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 9954 - 9958
[23] Solid-phase synthesis of C-terminal peptide amides from N-tetrachlorophthaloyl protected amino acids
Cros, E
Planas, M
Mejías, X
Bardají, E
TETRAHEDRON LETTERS, 2001, 42 (35) : 6105 - 6107
[24] Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handle
Guillaumie, F
Kappel, JC
Kelly, NM
Barany, G
Jensen, KJ
TETRAHEDRON LETTERS, 2000, 41 (32) : 6131 - 6135
[25] Side-chain anchoring strategy for solid-phase synthesis of peptide acids with C-terminal cysteine
Barany, G
Han, YX
Hargittai, B
Liu, RQ
Varkey, JT
BIOPOLYMERS, 2003, 71 (06) : 652 - 666
[26] Fmoc solid-phase synthesis of C-terminal thioesters peptide using an intramolecular N,S-acyl shift
Ollivier, N.
Behr, J. B.
El-Mahdi, O.
Blanpain, A.
Melnyk, O.
JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 130 - 130
[27] Solid-phase synthesis of a library of C-terminal agmatine dipeptides using a backbone amide linker (BAL) strategy
Ang, Melgious Jin Yan
Lim, Huichang Annie
Chia, Cheng San Brian
TETRAHEDRON LETTERS, 2012, 53 (41) : 5511 - 5514
[28] SOLID-PHASE SYNTHESIS OF PEPTIDES WITH C-TERMINAL ASPARAGINE OR GLUTAMINE - AN EFFECTIVE, MILD PROCEDURE BASED ON N-ALPHA-FLUORENYLMETHYLOXYCARBONYL (FMOC) PROTECTION AND SIDE-CHAIN ANCHORING TO A TRIS(ALKOXY)BENZYLAMIDE (PAL) HANDLE
ALBERICIO, F
VANABEL, R
BARANY, G
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1990, 35 (03): : 284 - 286
[29] Backbone Amide Linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides
Jensen, KJ
Alsina, J
Songster, MF
Vágner, J
Albericio, F
Barany, G
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) : 5441 - 5452
[30] Dihydropyran-2-carboxylic acid, a novel bifunctional linker for the solid-phase synthesis of peptides containing a C-terminal alcohol
Hsieh, HP
Wu, YT
Chen, ST
Wang, KT
CHEMICAL COMMUNICATIONS, 1998, (06) : 649 - 650

← 1 2 3 4 5 →