An amino acid N-derivatising group that can be coloured on demand

被引：3

作者：

Abell, AD ^{[1
]}

Martyn, DC ^{[1
]}

May, BCH ^{[1
]}

Nabbs, BK ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(02)00625-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method is presented whereby an amino acid is reacted with 5-formyl-1H-pyrrole-2-carboxylic acid to give an N-derivatised tag that has a latent ability to be coloured. A characteristic red pyrrolizin-3-one (coloured tag) is then revealed on treatment with hydrocinnamoyl chloride. This sequence has been carried out on amino acids in solution, and on solid phase, and also on dipeptides. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3673 / 3675

页数：3

共 10 条

[1]

ABELL AD, 1992, DETAILED REACTION ME, V2, P243

[2] PREPARATION AND REACTIONS OF TRIPHENYLARSORANYLIDENEKETENE [J].

BESTMANN, HJ ;

BANSAL, RK .

TETRAHEDRON LETTERS, 1981, 22 (39) :3839-3842

[3] Synthesis of pyrrolizin-3-ones by flash vacuum pyrolysis of pyrrol-2-ylmethylidene Meldrum's acid derivatives and 3-(pyrrol-2-yl)propenoic esters [J].

Campbell, SE ;

Comer, MC ;

Derbyshire, PA ;

Despinoy, XLM ;

McNab, H ;

Morrison, R ;

Sommerville, CC ;

Thornley, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (15) :2195-2202

[4] PRODUCTS FROM ATTEMPTED VILSMEIER-HAACK ACYLATIONS OF PYRROLES WITH SELECT AMIDES [J].

ERMILI, A ;

CASTRO, AJ ;

WESTFALL, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02) :339-&

[5] CYCLIC COMPOUNDS WITH HETERO-BRIDGE ATOMS .7. PYRROLIZIN-3-ONES [J].

FLITSCH, W ;

NEUMANN, U .

CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (07) :2170-&

[6]

Madder A, 1999, EUR J ORG CHEM, V1999, P2787

[7] PYRROLIZIN-3-ONES [J].

MCNAB, H ;

THORNLEY, C .

HETEROCYCLES, 1994, 37 (03) :1977-2008

[8] Discovery of sequence-selective peptide binding by synthetic receptors using encoded combinatorial libraries [J].

Still, WC .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :155-163

[9] Potentially macrocyclic peptidyl boronic acids as chymotrypsin inhibitors [J].

Tian, ZQ ;

Brown, BB ;

Mack, DP ;

Hutton, CA ;

Bartlett, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :514-522

[10]

WALLACE DM, 1994, J ORG CHEM, V59, P5230

← 1 →