Some influences of fluorine in bioorganic chemistry

被引:495
作者
OHagan, D [1 ]
Rzepa, HS [1 ]
机构
[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED, DEPT CHEM, LONDON SW7 2AY, ENGLAND
关键词
D O I
10.1039/a604140j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereochemical outcome on processing fluorinated substrate analogues by enzymes can often be controlled by electronic and stereoelectronic factors associated with the fluorine atom.
引用
收藏
页码:645 / 652
页数:8
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共 93 条
[1]   How strong is a pi-facial hydrogen bond? [J].
Adams, H ;
Harris, KDM ;
Hembury, GA ;
Hunter, CA ;
Livingstone, D ;
McCabe, JF .
CHEMICAL COMMUNICATIONS, 1996, (22) :2531-2532
[2]   DEHYDROGENATION OF A PHOSPHONATE SUBSTRATE ANALOG BY GLYCEROL 3-PHOSPHATE DEHYDROGENASE [J].
ADAMS, PR ;
HARRISON, R ;
INCH, TD .
BIOCHEMICAL JOURNAL, 1974, 141 (03) :729-732
[3]   BOND LENGTH AND REACTIVITY - THE GAUCHE EFFECT - A COMBINED CRYSTALLOGRAPHIC AND THEORETICAL INVESTIGATION OF THE EFFECTS OF BETA-SUBSTITUENTS ON C-OX BOND LENGTH [J].
AMOS, RD ;
HANDY, NC ;
JONES, PG ;
KIRBY, AJ ;
PARKER, JK ;
PERCY, JM ;
SU, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :549-558
[4]  
ANH NT, 1977, NOUV J CHIM, V1, P61
[5]   NON-ADDITIVE EFFECTS OF POLYSUBSTITUTION IN CH4 AND CH3 - A TEST OF ABINITIO AND SEMIEMPIRICAL MO METHODS [J].
BAIRD, NC .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (07) :1567-1572
[6]   STEREOCHEMICAL CONSEQUENCES OF ELECTRON DELOCALIZATION IN EXTENDED PI SYSTEMS - INTERPRETATION OF CIS EFFECT EXHIBITED BY 1,2-DISUBSTITUTED ETHYLENES AND RELATED PHENOMENA [J].
BINGHAM, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (02) :535-540
[7]  
BLACKBURN GM, 1981, CHEM IND-LONDON, P134
[8]   SYNTHESIS OF PHOSPHONATE ANALOGS OF 1,3-BISPHOSPHOGLYCERIC ACID AND THEIR BINDING TO YEAST PHOSPHOGLYCERATE KINASE [J].
BLACKBURN, GM ;
JAKEMAN, DL ;
IVORY, AJ ;
WILLIAMSON, MP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (21) :2573-2578
[9]   THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES [J].
BLACKBURN, GM ;
KENT, DE ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1119-1125
[10]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+