Substrate Specificities of Several Prenyl Chain Elongating Enzymes with Respect to 4-Methyl-4-pentenyl Diphosphate

In order to develop synthetic methods for biologically active homoallylic terpene sulfates, we examined the applicability and substrate specificities of several prenyl chain elongating enzymes with respect to 4-methyl-4-pentenyl diphosphate (homoIPP). The reaction of dimethylallyl diphosphate with h...

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Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2004-10, Vol.68 (10), p.2070-2075
Main Authors: NAGAKI, Masahiko, MIKI, Yohei, NAKADA, Minori, KAWAKAMI, Jun, KITAHARA, Haruo, MAKI, Yuji, GOTOH, Yoshinori, NISHINO, Tokuzo, KOYAMA, Tanetoshi
Format: Article
Language:English
Subjects:
Alkyl and Aryl Transferases - metabolism
Biological and medical sciences
farnesyl diphosphate synthase
Fundamental and applied biological sciences. Psychology
geranylgeranyl diphosphate synthase
Gram-Positive Bacteria - enzymology
Hemiterpenes - chemistry
Organophosphates - chemistry
prenyl chain elongating enzyme
Substrate Specificity
Sulfolobus acidocaldarius - enzymology
undecaprenyl diphosphate synthase
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Summary:In order to develop synthetic methods for biologically active homoallylic terpene sulfates, we examined the applicability and substrate specificities of several prenyl chain elongating enzymes with respect to 4-methyl-4-pentenyl diphosphate (homoIPP). The reaction of dimethylallyl diphosphate with homoIPP by use of Bacillus stearothermophilus (all-trans)-farnesyl diphosphate synthase resulted in efficient yields of cis-(yield: 45.9%) and trans-4,8-dimethylnona-3,7-dien-1-ol (homoGOH, 25.5%), which has a carbon skeleton of 4,8-dimethylnona-3-en-1-sulfate, an antiproliferative compound from a marine organism (Aiello, A. et al., Tetrahedron, 53, 11489-11492 (1997)). The homoIPP was found to be also active as a homoallylic substrate in place of isopentenyl diphosphate for Sulfolobus acidocaldarius geranylgeranyl diphosphate synthase to give diphosphate of cis- and trans-4,8,12-trimethyltrideca-3,7,11-trien-1-ol, for Micrococcus luteus B-P 26 hexaprenyl diphosphate synthase to give cis- and trans-4,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-ol (homoGGOH), and for Micrococcus luteus B-P 26 undecaprenyl diphosphate synthase to give cis-homoGGOH exclusively.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.68.2070