Premium
Antibiotics from Gliding Bacteria, LXXV. Absolute Configuration and Biosynthesis of Tartrolon B, a Boron‐Containing Macrodiolide from Sorangium cellulosum
Author(s) -
Schummer Dietmar,
Schomburg Dietmar,
Irschik Herbert,
Reichenbach Hans,
Höfle Gerhard
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960616
Subject(s) - absolute configuration , boron , chemistry , biosynthesis , stereochemistry , starter , substructure , bacteria , carbon fibers , organic chemistry , enzyme , biology , genetics , materials science , structural engineering , composite number , engineering , composite material , food science
The absolute configuration of tartrolon B ( 1 ), a boron‐containing macrodiolide from Sorangium cellulosum , was established by X‐ray structure analysis as (2 R ,3 R ,4 R ,7 S ,8 S ,11 S ). Compared to the related boron‐containing macrodiolides boromycin ( 2 ), aplasmomycin ( 3 ), and borophycin ( 4 ), and identical substructure and configuration of the boron‐binding site was found for all four compounds. The biosynthesis of 1 was investigated by feeding experiments with 13 C‐labeled precursors. According to NMR analyses, the carbon atoms from C‐1 to C‐18 are derived from acetate units, the two methyl groups at C‐22 and C‐23 are derived from methionine, and a three‐carbon starter unit C‐19 to C‐21 is derived from glycerol. The biosynthesis of 1 is closely related to those of 2 and 3 but with respect to the origin of the starter unit it is more distant to that of 4 .