THE BIOSYNTHESIS OF STREPTOTHRICIN-F .4. THE BIOSYNTHESIS OF THE STREPTOLIDINE MOIETY IN STREPTOTHRICIN-F

THE BIOSYNTHESIS OF STREPTOTHRICIN-F .4. THE BIOSYNTHESIS OF THE STREPTOLIDINE MOIETY IN STREPTOTHRICIN-F
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DOI:
10.1016/s0040-4020(01)88659-2
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发表时间:
1983-01-01
期刊:
影响因子:
2.1
通讯作者:
GOULD, SJ
GOULD, SJ
中科院分区:
化学3区
文献类型:
--
作者:
MARTINKUS, KJ;TANN, CH;GOULD, SJ

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合成了一系列以13C和15N或2H标记的精氨酸,并将其喂给链霉菌L-1689-23。分别用13C或2H NMR对分离得到的链霉素F进行分析,以确定得到的标记模式。精氨酸被代谢成β。-酮精氨酸,可能是通过磷酸吡哆醛加合物,然后通过环化、还原、重排和羟基化得到链苯胺部分。所描述的途径也可以解释其他已知抗生素和- β -羟基- γ的形成。胺基酸。
A series of arginines specifically labeled with 13C and 15N or with 2H were synthesized and fed to Streptomyces L-1689-23. The streptothricin F isolated in each case was analyzed by 13C or 2H NMR, respectively, in order to determine the labeling pattern obtained. Arginine is apparently metabolized to a .beta.-ketoarginine, possibly via a pyridoxal phosphate adduct, and then via cyclization, reduction, rearrangement and hydroxylation to the streptolidine moiety. The pathway described can also account for the formation of other known antibiotics and for .beta.-hydroxy-.gamma.-amino acids.