BIOSYNTHESIS OF PULVILLORIC ACID .I. PRODUCTION, ISOLATION, AND DEGRADATIONS
BIOSYNTHESIS OF PULVILLORIC ACID .I. PRODUCTION, ISOLATION, AND DEGRADATIONS
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DOI：
10.1021/bi00839a058
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发表时间：
1969-01-01
期刊：
影响因子：
2.9
通讯作者：
NAKAJIMA, S
中科院分区：
文献类型：
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作者：
TANENBAUM, SW;NAKAJIMA, S
一项对最大实验室产量的pulvilloric酸（一种由青霉菌产生的抗生素物质）所需的环境条件的研究，导致在固定培养物中的估计产量超过1.3 g/l。所需培养基为5%甘油-Czapek-Dox，添加0.1 ml玉米浆/l。发现分离和纯化步骤的改进克服了与这种代谢物有关的主要困难，即其不稳定性。本文提出了一种适合于放射性示踪实验的分步降解方法。该方法包括将pulvilloric酸水解成已知的1-（3-二羟基苯基）-2-庚醇，然后进行甲基化和脱水，得到1-（3，5-二甲氧基苯基）-1-庚烯。后一中间体是pX。胡维酸是由青霉菌产生的黄色抗真菌和抗细菌物质（Brian等人，1957年）。其分子结构（I）已通过降解测定（McOmie等人，1963，1966）和合成的（Bulli-more等人，1967）研究。无论是在生物成因和结构方面，pulvilloric酸非常类似于其他两个次级代谢产物。这些是桔霉素，其生物发生已经由几个小组研究出来（Birch等人，1958; Schwenk等人，1958; Rodig等人，1966），并已表明涉及乙酸盐-聚丙二酸盐单一碳转移途径;以及最近由Iwai和三岛（1965）表征的子囊壳碱。本文报道了菌株和发酵的改进，这些改进导致了一致的高产率的pulvilloric酸生产;并描述了获得分析纯抗生素的简便分离方法。作为一个初步的放射性示踪剂实验上的说明pulvilloric酸的生物合成，一个碳的碳降解程序，在每个阶段的中间体，具有令人满意的产量，已经开发。
A study of the environmental conditions needed for maximal laboratory yields of pulvilloric acid, an antibiotic substance produced by Penicillium pulvillorum, ledto the estimated production in stationary cultures of quantities over 1.3 g/1. The requisite medium is 5% glycerol-Czapek-Dox supplemented with 0.1 ml of corn steep liquor/1. Improvements in isolation and purification steps were found which overcame the major difficulty involved in work with this metabolite, ie, itsinstability. A completestepwise degradation procedure, adaptable for radioactive tracer experiments, was de-veloped. This process involved hydrolysis of pulvilloric acid into the known l-(3-dihydroxyphenyl)-2-heptanol, followed by methylation and dehydration which providedl-(3, 5-dimethoxyphenyl)-1-heptene. The latter intermediate was pX. ulvilloric acid is a yellow antifungal and antibacterial substance produced by Penicilliumpulvillorum (Brian et al., 1957). Its molecular structure (I) has been determined by degradative (McOmie et al., 1963, 1966) and synthetic (Bulli-more et al., 1967) studies. Both in biogenetic and structural terms, pulvilloric acid closely resembles two other secondary metabolites. These are citrinin, whose biogenesis has been worked out by several groups (Birch et al., 1958; Schwenk et al., 1958; Rodig et al., 1966) and has been shown to involve the acetate-polymalonate single carbon-transfer pathways; and ascochitine, more recently characterized by Iwai and Mishima (1965).This paper reports strain and fermentation improvements which have lead to consistent, high yield production of pulvilloric acid; anddescribes a facile isolation method for obtaining the analytically pure antibiotic. As a preliminary to radioactive tracer experiments on the elucidation of the biosynthesis of pulvilloric acid, a carbon-by-carbon degradative procedure, with satisfactory yields of intermediates at each stage, has been developed.