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Identification and Characterization of a Welwitindolinone Alkaloid Biosynthetic Gene Cluster in the Stigonematalean Cyanobacterium Hapalosiphon welwitschii
Author(s) -
Hillwig Matthew L.,
Fuhrman Heather A.,
Ittiamornkul Kuljira,
Sevco Tyler J.,
Kwak Daniel H.,
Liu Xinyu
Publication year - 2014
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201300794
Subject(s) - gene cluster , biosynthesis , biochemistry , o methyltransferase , gene , chemistry , biology , alkaloid , enzyme , glycosyltransferase , stereochemistry , methyltransferase , methylation
Abstract The identification of a 36 kb welwitindolinone ( wel ) biosynthetic gene cluster in Hapalosiphon welwitschii UTEX B1830 is reported. Characterization of the enzymes responsible for assembling the early biosynthetic intermediates geranyl pyrophosphate and 3‐(( Z )‐2′‐isocyanoethenyl)indole as well as a dedicated N‐methyltransferase in the maturation of N ‐methylwelwitindolinone C isothiocyanate solidified the link between the wel pathway and welwitindolinone biosynthesis. Comparative analysis of the ambiguine and welwitindolinone biosynthetic pathways in two different organisms provided insights into the origins of diverse structures within hapalindole‐type molecules.