Semipermanent C-Terminal Carboxylic Acid Protecting Group: Application to Solubilizing Peptides and Fragment Condensation

被引：18

作者：

Paradis-Bas, Marta ^{[1
,2
]}

Tulla-Puche, Judit ^{[1
,2
]}

Albericio, Fernando ^{[1
,2
,3
,4
,5
]}

机构：

[1] Inst Res Biomed IRB Barcelona Barcelon, Barcelona 08028, Spain

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

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

[4] Univ Kwazulu Natal, Sch Chem & Phys, ZA-4001 Durban, South Africa

[5] Yachay Tech, Sch Chem, Yachay City Of Knowledge 100119, Urcuqui, Ecuador

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 02期

关键词：

SOLID-PHASE SYNTHESIS; HYDROPHOBIC PEPTIDES; REDUCTION; AMIDES; BOND; TAG;

D O I：

10.1021/ol5033943

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-methoxy-4-methylsulfinylbenzyl alcohol (Mmsb-OH) safety-catch linker has been described as a useful tool to overcome two obstacles in peptide synthesis: the solubility and fragment condensation of peptides. The incorporation of the linker into an insoluble peptide target, thereby allowing the conjugation of a poly-Lys as a solubilizing tag, notably enhanced the solubility of the peptide. The selective conditions that remove that linker favored its incorporation as a semipermanent C-terminal protecting group, thereby allowing fragment condensation of peptides.

引用

页码：294 / 297

页数：4

共 28 条

[1] Solid-phase synthesis of C-terminal modified peptides
Alsina, J
Albericio, F
[J]. BIOPOLYMERS, 2003, 71 (04) : 454 - 477
[2] BARLOS K, 1991, INT J PEPT PROT RES, V37, P513
[3] Brichard M.-H., 2011, [No title captured], Patent No. [WO 2011006644 A2, 2011006644]
[4] Synthesis of hydrophobic peptides: An Fmoc "Solubilising Tail" method
Choma, CT
Robillard, GT
Englebretsen, DR
[J]. TETRAHEDRON LETTERS, 1998, 39 (16) : 2417 - 2420
[5] Self-assembling polymer-peptide conjugates: Nanostructural tailoring
Collier, JH
Messersmith, PB
[J]. ADVANCED MATERIALS, 2004, 16 (11) : 907 - 910
[6] Boc SPPS of two hydrophobic peptides using a ''solubilising tail'' strategy: Dodecaalanine and chemotactic protein 10(42-55)
Englebretsen, DR
Alewood, PF
[J]. TETRAHEDRON LETTERS, 1996, 37 (46) : 8431 - 8434
[7] The reduction of oxidized methionine residues in peptide thioesters with NH4I-Me2S
Hackenberger, Christian P. R.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) : 2291 - 2295
[8] Synthesis of an Arginine Tagged [Cys155-Arg180] Fragment of NY-ESO-1: Elimination of an Undesired By-product Using 'In House' Resins
Harris, Paul W. R.
Brimble, Margaret A.
[J]. SYNTHESIS-STUTTGART, 2009, (20): : 3460 - 3466
[9] Use of a Temporary "Solubilizing" Peptide Tag for the Fmoc Solid-Phase Synthesis of Human Insulin Glargine via Use of Regioselective Disulfide Bond Formation
Hossain, Mohammed Akhter
Belgi, Alessia
Lin, Feng
Zhang, Suode
Shabanpoor, Fazel
Chan, Linda
Belyea, Chris
Truong, Hue-Trung
Blair, Amy R.
Andrikopoulos, Sof
Tregear, Geoffrey W.
Wade, John D.
[J]. BIOCONJUGATE CHEMISTRY, 2009, 20 (07) : 1390 - 1396
[10] Self-Assembled Proteins and Peptides for Regenerative Medicine
Hosseinkhani, Hossein
Hong, Po-Da
Yu, Dah-Shyong
[J]. CHEMICAL REVIEWS, 2013, 113 (07) : 4837 - 4861

← 1 2 3 →