Cyclodextrins as NMR probes in the study of the enantiomeric compositions of N-benzyloxycarbonylamino-phosphonic and phosphinic acids

被引：14

作者：

Berlicki, L ^{[1
]}

Rudzinska, E ^{[1
]}

Mucha, A ^{[1
]}

Kafarski, P ^{[1
]}

机构：

[1] Wroclaw Univ Technol, Inst Organ Chem Biochem & Biotechnol, PL-50370 Wroclaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 10期

关键词：

D O I：

10.1016/j.tetasy.2004.03.037

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The inclusion complexes of alpha- and hydroxypropyl-gamma-cyclodextrins with N-benzyloxycarbonyl protected alpha-aminophosphonic and alpha-aminophosphinic acids were studied by means of NMR spectroscopy. Cyclodextrins appear to be a useful tool for determining the enantiomeric excess of all the examined amino acid mimetics. Stoichiometry and geometry of selected complexes were investigated. 2D ROESY experiments and Continuous variation methods indicated that there are three possible types of complexation: two of guest/host ratio being 1:1 and one of 1:2 stoichiometry. Molecular modelling studies confirmed the proposed modes of complexation. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1597 / 1602

页数：6

共 57 条

[1]

BAEWSKA K, 2002, TETRAHEDRON-ASYMMETR, V13, P671

[2] EVALUATION OF INTRINSIC BINDING-ENERGY FROM A HYDROGEN-BONDING GROUP IN AN ENZYME-INHIBITOR [J].

BARTLETT, PA ;

MARLOWE, CK .

SCIENCE, 1987, 235 (4788) :569-571

[3] PHOSPHORUS-CONTAINING PEPTIDE ANALOGS AS PEPTIDASE INHIBITORS [J].

BARTLETT, PA ;

MARLOWE, CK ;

GIANNOUSIS, PP ;

HANSON, JE .

COLD SPRING HARBOR SYMPOSIA ON QUANTITATIVE BIOLOGY, 1987, 52 :83-90

[4] 1-AMINOALKYLPHOSPHONOUS ACIDS .1. ISOSTERES OF THE PROTEIN AMINO-ACIDS [J].

BAYLIS, EK ;

CAMPBELL, CD ;

DINGWALL, JG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2845-2853

[5] Enantiodifferentiation of aminophosphonic and aminophosphinic acids with α- and β-cyclodextrins [J].

Berlicki, L ;

Rudzinska, E ;

Kafarski, P .

TETRAHEDRON-ASYMMETRY, 2003, 14 (11) :1535-1539

[6] ALKYLATION OF CHIRAL PHOSPHONOGLYCINE EQUIVALENTS - ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES [J].

CABELLA, G ;

JOMMI, G ;

PAGLIARIN, R ;

SELLO, G ;

SISTI, M .

TETRAHEDRON, 1995, 51 (06) :1817-1826

[7] CHIRAL RECOGNITION OF STRUCTURALLY RELATED AMINOALKYLPHOSPHONIC ACID-DERIVATIVES ON AN ACETYLATED BETA-CYCLODEXTRIN-BONDED PHASE [J].

CAMILLERI, P ;

REID, CA ;

MANALLACK, DT .

CHROMATOGRAPHIA, 1994, 38 (11-12) :771-775

[8] Phosphinic acid compounds in biochemistry, biology and medicine [J].

Collinsová, M ;

Jirácek, J .

CURRENT MEDICINAL CHEMISTRY, 2000, 7 (06) :629-647

[9] Asymmetric synthesis of aziridine 2-phosphonates and azirinyl phosphonates from enantiopure sulfinimines [J].

Davis, FA ;

McCoull, W .

TETRAHEDRON LETTERS, 1999, 40 (02) :249-252

[10] Phosphinic peptide inhibitors as tools in the study of the function of zinc metallopeptidases [J].

Dive, V ;

Lucet-Levannier, K ;

Georgiadis, D ;

Cotton, J ;

Vassiliou, S ;

Cuniasse, P ;

Yiotakis, A .

BIOCHEMICAL SOCIETY TRANSACTIONS, 2000, 28 :455-460

← 1 2 3 4 5 6 →