Synthesis of Potential Early-Stage Intermediates in the Biosynthesis of FR900482 and Mitomycin C
Synthesis of Potential Early-Stage Intermediates in the Biosynthesis of FR900482 and Mitomycin C
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DOI：
10.1021/ol802631c
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发表时间：
2009-02-19
期刊：
影响因子：
5.2
通讯作者：
Williams, Robert M.
中科院分区：
文献类型：
--
作者：
Chamberland, Stephen;Grueschow, Sabine;Williams, Robert M.
除了鉴定3-氨基-5-羟基苯甲酸（AHBA）和D-葡糖胺作为丝裂霉素C（5）和FR 900482（6）的生物合成前体外，对自然用于制备这些抗肿瘤抗生素的途径知之甚少。为了深入了解它们的生物合成，制备了氨基酸1和2以及C-2 M-乙酰化衍生物3和4。这些推定的生物合成中间体和N-乙酰基半胱胺硫酯类似物28和29的制备应该能够确认它们参与FR 900482和丝裂霉素C的生物合成。
Beyond the identification of 3-amino-5-hydroxybenzoic acid (AHBA) and D-glucosamine as biosynthetic precursors to mitomycin C (5) and FR900482 (6), little is known about the pathway Nature uses to prepare these antitumor antibiotics. To gain some insight into their biosynthesis, amino acids 1 and 2 as well as C-2 M-acetylated derivatives 3 and 4 were prepared. Preparation of these putative biosynthetic intermediates and N-acetylcysteamine thioester analogues 28 and 29 should enable confirmation of their involvement in FR900482 and mitomycin C biosynthesis.