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Efficient synthesis of 13 C‐labelled erythromycin biosynthetic intermediate. 1: S ‐2‐acetylaminoethyl (2 R ,3 R ,4 R ,5 R )‐3,5‐diacetoxy‐2,4‐dimethyl‐4‐([ 13 C]methoxy)‐heptanethioate
Author(s) -
Iida Katsumi,
Kajiwara Masahiro,
InoueTanihata Tomoko,
Fukui Mineo,
Nakata Tadashi,
Oishi Takeshi
Publication year - 2008
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1507
Subject(s) - chemistry , erythromycin , biosynthesis , stereochemistry , elongation , labelling , antibiotics , biochemistry , enzyme , metallurgy , ultimate tensile strength , materials science
An efficient 13 C‐labelling synthesis of the putative erythromycin biosynthetic intermediate, S ‐2‐acetylaminoethyl (2 R ,3 R ,4 R ,5 R )‐3,5‐diacetoxy‐2,4‐dimethyl‐4‐([ 13 C]methoxy)heptanethioate, which would be useful for the investigation of the chain elongation mechanism in erythromycin biosynthesis, was achieved by utilizing iodo[ 13 C]methane and (2 S ,3 R ,4 R ,5 R )‐4‐hydroxy‐3,5‐ O ‐isopropylidene‐2,4‐dimethylheptanol, obtained in our previous studies on erythromycin A synthesis. Copyright © 2008 John Wiley & Sons, Ltd.