A novel, base-labile fluorous amine protecting group: synthesis and use as a tag in the purification of synthetic peptides

被引：51

作者：

de Visser, PC

van Helden, M

Filippov, DV

van der Marel, GA

Drijfhout, JW

van Boom, JH

Noort, D

Overkleeft, HS

机构：

[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

[2] Leiden Univ, Ctr Med, NL-2300 RC Leiden, Netherlands

[3] TNO, Prins Maurits Lab, NL-2280 AA Rijswijk, Netherlands

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 50期

关键词：

fluorous; Msc protecting group; synthetic peptides; purification;

D O I：

10.1016/j.tetlet.2003.09.220

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, base-labile fluorous tag based on the Msc amine protecting group was synthesized. Its use in the purification of synthetic peptides by fluorous HPLC or fluorous SPE was demonstrated. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9013 / 9016

页数：4

共 31 条

[1] Chemical protein synthesis by solid phase ligation of unprotected peptide segments [J].

Canne, LE ;

Botti, P ;

Simon, RJ ;

Chen, YJ ;

Dennis, EA ;

Kent, SBH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8720-8727

[2] Synthesis and reactions of fluorous carbobenzyloxy (FCbz) derivatives of α-amino acids [J].

Curran, DP ;

Amatore, M ;

Guthrie, D ;

Campbell, M ;

Go, E ;

Luo, ZY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4643-4647

[3] Thiol additions to acrylates by fluorous mixture synthesis: relative control of elution order in demixing by the fluorous tag and the thiol substituent [J].

Curran, DP ;

Oderaotoshi, Y .

TETRAHEDRON, 2001, 57 (24) :5243-5253

[4] Fluorous synthesis with fewer fluorines (light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel [J].

Curran, DP ;

Luo, ZY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9069-9072

[5] Preparation of a fluorous benzyl protecting group and its use in a fluorous synthesis approach to a disaccharide [J].

Curran, DP ;

Ferritto, R ;

Hua, Y .

TETRAHEDRON LETTERS, 1998, 39 (28) :4937-4940

[6]

DIAZ J, 1985, EUR J MED CHEM, V20, P219

[7]

FILIPPOV D, 1994, SYNLETT, P922

[8] Use of benzyloxycarbonyl (Z)-based fluorophilic tagging reagents in the purification of synthetic peptides [J].

Filippov, DV ;

van Zoelen, DJ ;

Oldfield, SP ;

van der Marel, GA ;

Overkleeft, HS ;

Drijfhout, JW ;

van Boom, JH .

TETRAHEDRON LETTERS, 2002, 43 (43) :7809-7812

[9] Introduction - Fluorous chemistry: from biphasic catalysis to a parallel chemical universe and beyond [J].

Gladysz, JA ;

Curran, DP .

TETRAHEDRON, 2002, 58 (20) :3823-3825

[10] Protein synthesis by native chemical ligation: Expanded scope by using straightforward methodology [J].

Hackeng, TM ;

Griffin, JH ;

Dawson, PE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (18) :10068-10073

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