THE EFFICIENT SYNTHESIS AND SIMPLE RESOLUTION OF A PROLINEBORONATE ESTER SUITABLE FOR ENZYME-INHIBITION STUDIES

被引:43
作者
KELLY, TA
FUCHS, VU
PERRY, CW
SNOW, RJ
机构
关键词
D O I
10.1016/S0040-4020(01)86281-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the preparation and resolution of the pinanediol ester of prolineboronic acid is described. The method takes advantage of the ease of both the lithiation and the reduction of boc-pyrrole to generate the desired compound rapidly and in high yield.
引用
收藏
页码:1009 / 1016
页数:8
相关论文
共 26 条
[1]   B-11 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE STRUCTURE OF THE TRANSITION-STATE ANALOG PHENYLBORONIC ACID BOUND TO CHYMOTRYPSIN [J].
ADEBODUN, F ;
JORDAN, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) :309-310
[2]  
BACHOVCHIN WW, 1990, J BIOL CHEM, V265, P3738
[3]   N-15 NMR-SPECTROSCOPY OF THE CATALYTIC-TRIAD HISTIDINE OF A SERINE PROTEASE IN PEPTIDE BORONIC ACID INHIBITOR COMPLEXES [J].
BACHOVCHIN, WW ;
WONG, WYL ;
FARRJONES, S ;
SHENVI, AB ;
KETTNER, CA .
BIOCHEMISTRY, 1988, 27 (20) :7689-7697
[4]  
BACHOVCHIN WW, 1989, Patent No. 3223
[5]   B-11 NMR-STUDIES OF AN ARYL BORONIC ACID BOUND TO CHYMOTRYPSIN AND SUBTILISIN [J].
BALDWIN, JE ;
CLARIDGE, TDW ;
DEROME, AE ;
SCHOFIELD, CJ ;
SMITH, BD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (01) :9-12
[6]   SERINE PROTEASE MECHANISM - STRUCTURE OF AN INHIBITORY COMPLEX OF ALPHA-LYTIC PROTEASE AND A TIGHTLY BOUND PEPTIDE BORONIC ACID [J].
BONE, R ;
SHENVI, AB ;
KETTNER, CA ;
AGARD, DA .
BIOCHEMISTRY, 1987, 26 (24) :7609-7614
[7]   STRUCTURAL-ANALYSIS OF SPECIFICITY - ALPHA-LYTIC PROTEASE COMPLEXES WITH ANALOGS OF REACTION INTERMEDIATES [J].
BONE, R ;
FRANK, D ;
KETTNER, CA ;
AGARD, DA .
BIOCHEMISTRY, 1989, 28 (19) :7600-7609
[8]   ORGANOBORANES .30. CONVENIENT PROCEDURES FOR THE SYNTHESIS OF ALKYLBORONIC AND ALKENYLBORONIC ACIDS AND ESTERS [J].
BROWN, HC ;
BHAT, NG ;
SOMAYAJI, V .
ORGANOMETALLICS, 1983, 2 (10) :1311-1316
[9]   ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].
BROWN, HC ;
COLE, TE .
ORGANOMETALLICS, 1983, 2 (10) :1316-1319
[10]   CRYSTAL VERSUS SOLUTION STRUCTURE OF ENZYMES - NMR-SPECTROSCOPY OF A PEPTIDE BORONIC ACID-SERINE PROTEASE COMPLEX IN THE CRYSTALLINE STATE [J].
FARRJONES, S ;
SMITH, SO ;
KETTNER, CA ;
GRIFFIN, RG ;
BACHOVCHIN, WW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (18) :6922-6924