ANTIBODY-CATALYZED CATIONIC CYCLIZATION

被引:71
作者
LI, TY
JANDA, KD
ASHLEY, JA
LERNER, RA
机构
[1] SCRIPPS RES INST, DEPT MOLEC BIOL, LA JOLLA, CA 92037 USA
[2] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
关键词
D O I
10.1126/science.8191282
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Two major goals for the design of new catalysts are the facilitation of chemical transformations and control of product outcome. An antibody has been induced that efficiently catalyzes a cationic cyclization in which an acyclic olefinic sulfonate ester substrate is converted almost exclusively (98 percent) to a cyclic alcohol. The key to the catalysis of the reaction and the restriction of the product complexity is the use of antibody binding energy to rigidly enforce a concerted mechanism in accord with the design of the hapten. Thus, the ability to direct binding energy allows the experimenter to dictate a reaction mechanism which is an otherwise difficult task in chemistry. New catalysts, for cationic cyclization may be of general use in the formation of carbon-carbon and carbon-heteroatom bonds leading to multiring molecules including steroids and heterocyclic compounds.
引用
收藏
页码:1289 / 1293
页数:5
相关论文
共 43 条
[21]   NONENZYMIC BIOGENETIC-LIKE OLEFINIC CYCLIZATIONS [J].
JOHNSON, WS .
ACCOUNTS OF CHEMICAL RESEARCH, 1968, 1 (01) :1-&
[22]  
JOHNSON WS, 1987, J AM CHEM SOC, V109, P5582
[23]  
JOHNSON ZBW, 1964, J AM CHEM SOC, V86, P1959
[24]  
KASANO M, 1991, CHEM PHARM BULL, V39, P239
[25]  
KATRITZKY AR, 1992, HETEROCYCLES, V33, P1011
[26]   CLONING AND CHARACTERIZATION OF THE 2,3-OXIDOSQUALENE CYCLASE-CODING GENE OF CANDIDA-ALBICANS [J].
KELLY, R ;
MILLER, SM ;
LAI, MH ;
KIRSCH, DR .
GENE, 1990, 87 (02) :177-183
[27]   CONTINUOUS CULTURES OF FUSED CELLS SECRETING ANTIBODY OF PREDEFINED SPECIFICITY [J].
KOHLER, G ;
MILSTEIN, C .
NATURE, 1975, 256 (5517) :495-497
[28]   CONFIGURATION OF RING NITROGEN IN N-OXIDES AND CONFORMATION OF TROPANES .18. [J].
MANDAVA, N ;
FODOR, G .
CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (17) :2761-&
[29]  
MARCH J, 1985, ADV ORG CHEM, P312
[30]   1,2-METHYL SHIFTS IN THE CYCLIZATION OF SQUALENE TO LANOSTEROL [J].
MAUDGAL, RK ;
TCHEN, TT ;
BLOCH, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (10) :2589-2590