EPSP SYNTHASE INHIBITOR DESIGN .2. THE IMPORTANCE OF THE 3-PHOSPHATE GROUP FOR LIGAND-BINDING AT THE SHIKIMATE-3-PHOSPHATE SITE AND THE IDENTIFICATION OF 3-MALONATE ETHERS AS NOVEL 3-PHOSPHATE MIMICS

被引：17

作者：

MILLER, MJ

ANDERSON, KS

BRACCOLINO, DS

CLEARY, DG

GRUYS, KJ

HAN, CY

LIN, KC

PANSEGRAU, PD

REAM, JE

SAMMONS, RD

SIKORSKI, JA

机构：

[1] MONSANTO CORP RES,UNIT MONSANTO CO,700 CHESTERFIELD PKWY N,ST LOUIS,MO 63198

[2] MONSANTO CORP RES,DIV NEW PROD,AGR GRP,ST LOUIS,MO 63198

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 07期

关键词：

D O I：

10.1016/S0960-894X(01)80425-X

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Studies using alternate substrates, inhibitor product mimics and new derivatives of 4,5-dideoxy-shikimate-3-phosphate (ddS3P) are reported which indicate that the 3-phosphate group contributes significantly to substrate and inhibitor recognition at the shikimate 3-phosphate (S3P) site and that 3-malonate ethers will function as suitable 3-phosphate replacements for substrate and inhibitor binding to the S3P site of this enzyme.

引用

页码：1435 / 1440

页数：6

共 25 条

[1] INHIBITION OF EPSP SYNTHASE BY ANALOGS OF THE TETRAHEDRAL INTERMEDIATE AND OF EPSP
ALBERG, DG
LAUHON, CT
NYFELER, R
FASSLER, A
BARTLETT, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) : 3535 - 3546
[2] THE SITE OF THE INHIBITION OF THE SHIKIMATE PATHWAY BY GLYPHOSATE .2. INTERFERENCE OF GLYPHOSATE WITH CHORISMATE FORMATION INVIVO AND INVITRO
AMRHEIN, N
DEUS, B
GEHRKE, P
STEINRUCKEN, HC
[J]. PLANT PHYSIOLOGY, 1980, 66 (05) : 830 - 834
[3] OBSERVATION BY C-13 NMR OF THE EPSP SYNTHASE TETRAHEDRAL INTERMEDIATE BOUND TO THE ENZYME ACTIVE-SITE
ANDERSON, KS
SAMMONS, RD
LEO, GC
SIKORSKI, JA
BENESI, AJ
JOHNSON, KA
[J]. BIOCHEMISTRY, 1990, 29 (06) : 1460 - 1465
[4] ISOLATION AND STRUCTURAL ELUCIDATION OF THE TETRAHEDRAL INTERMEDIATE IN THE EPSP SYNTHASE ENZYMATIC PATHWAY
ANDERSON, KS
SIKORSKI, JA
BENESI, AJ
JOHNSON, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) : 6577 - 6579
[5] ANDERSON KS, 1990, J BIOL CHEM, V265, P5567
[6] A TETRAHEDRAL INTERMEDIATE IN THE EPSP SYNTHASE REACTION OBSERVED BY RAPID QUENCH KINETICS
ANDERSON, KS
SIKORSKI, JA
JOHNSON, KA
[J]. BIOCHEMISTRY, 1988, 27 (19) : 7395 - 7406
[7] KINETIC AND STRUCTURAL-ANALYSIS OF ENZYME INTERMEDIATES - LESSONS FROM EPSP SYNTHASE
ANDERSON, KS
JOHNSON, KA
[J]. CHEMICAL REVIEWS, 1990, 90 (07) : 1131 - 1149
[8] EVALUATION OF 5-ENOLPYRUVOLYSHIKIMATE-3-PHOSPHATE SYNTHASE SUBSTRATE AND INHIBITOR BINDING BY STOPPED-FLOW AND EQUILIBRIUM FLUORESCENCE MEASUREMENTS
ANDERSON, KS
SIKORSKI, JA
JOHNSON, KA
ANDERSON, KS
JOHNSON, KA
[J]. BIOCHEMISTRY, 1988, 27 (05) : 1604 - 1610
[9] MECHANISM OF ENOLPYRUVYL SHIKIMATE-3-PHOSPHATE SYNTHASE EXCHANGE OF PHOSPHOENOLPYRUVATE WITH SOLVENT PROTONS
ANTON, DL
HEDSTROM, L
FISH, SM
ABELES, RH
[J]. BIOCHEMISTRY, 1983, 22 (25) : 5903 - 5908
[10] TOTAL SYNTHESIS OF (+/-)-METHYL SHIKIMATE AND (+/-)-3-PHOSPHOSHIKIMIC ACID
BARTLETT, PA
MCQUAID, LA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) : 7854 - 7860

← 1 2 3 →