Hapalindole/Ambiguine Biogenesis Is Mediated by a Cope Rearrangement, C-C Bond-Forming Cascade

Journal of the American Chemical Society

Volumn 137, Issue 49, 2015, Pages 15366-15369

  Li, Shasha ^a,b   Lowell, Andrew N ^a   Yu, Fengan ^a   Raveh, Avi ^a   Newmister, Sean A ^a   Bair, Nathan ^e   Schaub, Jeffrey M ^a   Williams, Robert M ^e,f   Sherman, David H ^a,b,c,d  

^a Life Sciences Institute   (United States)

^b Department of Medicinal Chemistry ^*  (United States)

^c UNIVERSITY OF MICHIGAN   (United States)

^d UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^e Veterinary Dentistry and Oral Surgery   (United States)

^f UNIVERSITY OF COLORADO CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BIOCHEMISTRY; CYCLIZATION; GENE ENCODING; POLYCYCLIC AROMATIC HYDROCARBONS; SUBSTITUTION REACTIONS;

AROMATIC SUBSTITUTION REACTIONS; ASSEMBLY MECHANISM; C-C BOND FORMING; COPE REARRANGEMENT; CYANOBACTERIUM; INDOLE ALKALOIDS; POLYCYCLIC RING SYSTEMS; PRENYLTRANSFERASES;

BIOSYNTHESIS;

AMBIGUINE; CARBON; DIMETHYLALLYLTRANSFERASE; FAMC1 PROTEIN; FAMD1 PROTEIN; FAMD2 PROTEIN; HAPALINDOLE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; AMBIGUINE G; HAPALINDOLE A; INDOLE ALKALOID;

ARTICLE; BIOGENESIS; BIOSYNTHESIS; CHEMICAL BOND; CONTROLLED STUDY; COPE REARRANGEMENT; CYCLIZATION; ELECTROPHILICITY; ENZYME ANALYSIS; FISCHERELLA; GEL ELECTROPHORESIS; GENE CLUSTER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PH; PRENYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SUPERNATANT; AMINO ACID SEQUENCE; CHEMICAL STRUCTURE; CHEMISTRY; CYANOBACTERIUM; GENETICS; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY;

AMINO ACID SEQUENCE; CYANOBACTERIA; INDOLE ALKALOIDS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MULTIGENE FAMILY;

EID: 84950240808     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b10136     Document Type: Article

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