Phosphorolytic reactivity of o-iodosylcarboxylates and related nucleophiles

被引:186
作者
Morales-Rojas, H [1 ]
Moss, RA [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Biol Chem, New Brunswick, NJ 08903 USA
关键词
D O I
10.1021/cr9405462
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Iodosyl- and iodylcarboxylate derivatives are effective reagents for the hydrolytic cleavage of fluorophosphonate nerve agents as well as certain insecticides and phosphate triester simulants. Many iodosyl- and iodylcarboxylate derivatives and various delivery systems have been prepared and tested against a variety of phosphate triesters and phosphonate diesters. True turnover capability under mild conditions is the most important feature of IBA-related systems in comparison with other nucleophiles that only react stoichiometrically.
引用
收藏
页码:2497 / 2521
页数:25
相关论文
共 226 条
[2]   Hydrolysis of phosphotriesters: Determination of transition states in parallel reactions by heavy-atom isotope effects [J].
Anderson, MA ;
Shim, H ;
Raushel, FM ;
Cleland, WW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9246-9253
[3]  
Andreopoulos FM, 1999, BIOTECHNOL BIOENG, V65, P579, DOI 10.1002/(SICI)1097-0290(19991205)65:5<579::AID-BIT11>3.3.CO
[4]  
2-P
[5]  
[Anonymous], 1991, ORGANIC PHOSPHORUS P
[6]   REACTIONS OF ORGANIC PHOSPHATES .5. HYDROLYSIS OF TRIPHENYL AND TRIMETHYL PHOSPHATES [J].
BARNARD, PW ;
VERNON, CA ;
LLEWELLYN, DR ;
WELCH, VA ;
BUNTON, CA .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JUL) :2670-&
[7]   SINGLE TRANSITION-STATE IN THE TRANSFER OF A NEUTRAL PHOSPHORYL GROUP BETWEEN PHENOXIDE ION NUCLEOPHILES IN AQUEOUS-SOLUTION [J].
BASAIF, SA ;
WARING, MA ;
WILLIAMS, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8115-8120
[8]   CRYSTAL-STRUCTURE AND I-127 MOSSBAUER SPECTRUM OF DIPHENYLIODONIUM-2-CARBOXYLATE HYDRATE, C13H9IO2.H2O - SECONDARY VS HYDROGEN-BONDING [J].
BATCHELOR, RJ ;
BIRCHALL, T ;
SAWYER, JF .
INORGANIC CHEMISTRY, 1986, 25 (09) :1415-1420
[9]   3-DIMENSIONAL STRUCTURE OF THE BINUCLEAR METAL CENTER OF PHOSPHOTRIESTERASE [J].
BENNING, MM ;
KUO, JM ;
RAUSHEL, FM ;
HOLDEN, HM .
BIOCHEMISTRY, 1995, 34 (25) :7973-7978
[10]   High resolution X-ray structures of different metal-substituted forms of phosphotriesterase from Pseudomonas diminuta [J].
Benning, MM ;
Shim, H ;
Raushel, FM ;
Holden, HM .
BIOCHEMISTRY, 2001, 40 (09) :2712-2722