A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols

被引：85

作者：

Baxendale, Ian R. ^{[1
]}

Ley, Steven V. ^{[1
]}

Smith, Christopher D. ^{[1
]}

Tranmer, Geoffrey K. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 46期

关键词：

D O I：

10.1039/b612197g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general flow process for the multi-step assembly of peptides has been developed and this procedure has been used to successfully construct a series of Boc, Cbz and Fmoc N-protected dipeptides in excellent yields and purities, including an extension of the method to enable the preparation of a tripeptide derivative.

引用

页码：4835 / 4837

页数：3

共 17 条

[1] AUTOMATED CONTINUOUS-FLOW PEPTIDE-SYNTHESIS [J].

ANDREWS, RP .

NATURE, 1986, 319 (6052) :429-430

[2] Total chemical synthesis of crambin [J].

Bang, D ;

Chopra, N ;

Kent, SBH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1377-1383

[3]

BAUMANN M, 2006, IN PRESS ORG LETT

[4] A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly [J].

Baxendale, Ian R. ;

Deeley, Jon ;

Griffiths-Jones, Charlotte M. ;

Ley, Steven V. ;

Saaby, Steen ;

Tranmer, Geoffrey K. .

CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568

[5] Preparation of the neolignan natural product grossamide by a continuous-flow process [J].

Baxendale, IR ;

Griffiths-Jones, CM ;

Ley, SV ;

Tranmer, GK .

SYNLETT, 2006, (03) :427-430

[6] Polymer-bound TBTU as a new solid-supported reagent for peptide synthesis [J].

Chinchilla, R ;

Dodsworth, DJ ;

Nájera, C ;

Soriano, JM .

TETRAHEDRON LETTERS, 2000, 41 (14) :2463-2466

[7] Depsipeptide methodology for solid-phase peptide synthesis:: Circumventing side reactions and development of an automated technique via depsidipeptide units [J].

Coin, Irene ;

Doelling, Rudolf ;

Krause, Eberhard ;

Bienert, Michael ;

Beyermann, Michael ;

Sferdean, Calin Dan ;

Carpino, Louis A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6171-6177

[8] OXYBENZOTRIAZOLE FREE PEPTIDE COUPLING REAGENTS FOR N-METHYLATED AMINO-ACIDS [J].

COSTE, J ;

FREROT, E ;

JOUIN, P ;

CASTRO, B .

TETRAHEDRON LETTERS, 1991, 32 (17) :1967-1970

[9] Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis [J].

Franckevicius, V ;

Knudsen, KR ;

Ladlow, M ;

Longbottom, DA ;

Ley, SV .

SYNLETT, 2006, (06) :889-892

[10] Recent progress of the synthetic studies of biologically active marine cyclic peptides and depsipeptides [J].

Hamada, Y ;

Shioiri, T .

CHEMICAL REVIEWS, 2005, 105 (12) :4441-4482

← 1 2 →