Improved synthesis of C-terminal peptide thioesters on "safety-catch" resins using LiBr/THF

被引：37

作者：

Quaderer, R ^{[1
]}

Hilvert, D ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Organ Chem Lab, ETH, CH-8092 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol016492h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS The alkanesulfonamide "safety-catch" resin has proven useful for Fmoc-based synthesis of C-terminal peptide thioesters. We now report that the yield of isolated thioester can increase significantly when the cleavage reaction is carried out in 2 M LiBr/THF rather than DMF or THE The largest effects are seen with problematic peptides that aggregate or form secondary structures on the resin.

引用

页码：3181 / 3184

页数：4

共 50 条

[1] Chemoenzymatic synthesis of C-terminal peptide thioesters for chemoselective ligations
Merkx, Remco
Quaedflieg, Peter
JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 3 - 4
[2] Total chemical synthesis of interferon-alpha using long peptide thioesters prepared by FMOC synthesis on a safety-catch resin
Strong, AE
BIOPOLYMERS, 2003, 71 (03) : 348 - 348
[3] TERA-linker: Safety-catch linker for peptide thioesters via Fmoc solid-phase synthesis
Rasmussen, J. E.
Hoeg-Jensen, T.
Jensen, K. J.
JOURNAL OF PEPTIDE SCIENCE, 2010, 16 : 72 - 73
[4] SAFETY-CATCH PROTECTING GROUPS IN PEPTIDE-SYNTHESIS
PATEK, M
LEBL, M
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1992, 57 (03) : 508 - 524
[5] Safety-catch linkers for Fmoc solid-phase synthesis of peptide thioesters and hydrazides by amide-to-imide activation
Paprocki, Maciej P.
Rasmussen, Jakob E.
Sorensen, Kasper K.
Jensen, Knud J.
JOURNAL OF PEPTIDE SCIENCE, 2021, 27 (12)
[6] Synthesis of peptide amides on safety-catch resin with microwave irradiation
Park, Jun-won
Lee, Keun-Hyeung
Bulletin of the Korean Chemical Society, 2009, 30 (10) : 2475 - 2478
[7] Synthesis of Peptide Amides on Safety-catch Resin with Microwave Irradiation
Park, Jun-won
Lee, Keun-Hyeung
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (10): : 2475 - 2478
[8] Safety-Catch Linkers for Solid-Phase Peptide Synthesis
Noki, Sikabwe
de la Torre, Beatriz G.
Albericio, Fernando
MOLECULES, 2024, 29 (07):
[9] Multiple condensations of peptide thioesters prepared by the "safety-catch" resin approach: Synthesis of p53 (303-393)
Teruya, Kenta
Mazur, Sharlyn
Appella, Ettore
PEPTIDE REVOLUTION: GENOMICS, PROTEOMICS & THERAPEUTICS, 2004, : 127 - 128
[10] Fmoc-compatible solid-phase peptide synthesis of long C-terminal peptide thioesters
Sewing, A
Hilvert, D
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (18) : 3395 - +

← 1 2 3 4 5 →