Biocatalytic and chemical routes to all the stereoisomers of methionine and ethionine sulfoxides
Biocatalytic and chemical routes to all the stereoisomers of methionine and ethionine sulfoxides
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DOI：
10.1016/s0957-4166(99)00271-2
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发表时间：
1999-07-30
影响因子：
--
通讯作者：
Brown, FM
中科院分区：
文献类型：
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作者：
Holland, HL;Andreana, PR;Brown, FM
球孢白僵菌ATCC7159或Caledonica ATCC 64970对D-和L-蛋氨酸的N-邻苯二甲酰基衍生物和D-和L-乙硫氨酸的N-邻苯二甲酰基衍生物进行生物转化，以高产率和非对映异构体过剩的方式产生相应的(S-S)亚硫醚。通过生物转化萃取物的结晶可以从L系列底物中获得纯的非对映异构体，通过生物转化萃取物的层析可以从D系列底物中获得相应的非对映异构体。在过氧化氢催化下，D-蛋氨酸和L-蛋氨酸的N-邻苯二甲酰基衍生物以及D-和L-乙硫氨酸的N-邻苯二甲酰基衍生物生成非对映异构体混合物，其中非对映异构体可通过结晶得到(SSSC)和(RSRC)非对映异构体，而(SSRC)和(RSSC)非对映异构体可通过层析得到。N-CBZ-和N-t-Boc蛋氨酸也被球孢杆菌和加氏芽孢杆菌转化为以S-S构型为主的亚硫醚，但分离的产率和D.E.从非对映异构体中脱除N-邻苯二甲酰基，高产率地得到相应的氨基酸亚砜；从受保护的蛋氨酸亚砜中脱除N-CBZ和N-t-Boc基团，且不损失硫磺的构型。(C)1994爱思唯尔科学有限公司。保留所有权利。
Biotransformations of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine by Beauveria bassiana ATCC 7159 or Beauveria caledonica ATCC 64970 produce the corresponding (S-S) sulfoxides in good yield and diastereomeric excess. Pure (SSSC) diastereomers can be obtained from L-series substrates by crystallisation of the biotransformation extract, and the corresponding (SSRC) products obtained from D-series substrates by chromatography of the biotransformation extract. Hydrogen peroxide-catalysed oxidation of the N-phthaloyl derivatives of D- and L-methionine and of D- and L-ethionine gives diastereomeric mixtures from which the (SSSC) and (RSRC) diastereomers can be obtained by crystallisation, and the (SSRC) and (RSSC) diastereomers obtained by chromatography. N-Cbz- and N-t-Boc methionines are also converted to sulfoxides with predominant (S-S) configuration by both B, bassiana and B. caledonica, but the isolated yields and d.e. of products were generally lower than those obtained from the N-phthaloyl substrates.Removal of the N-phthaloyl group from diastereomerically pure methionine and ethionine sulfoxides gave the corresponding amino acid sulfoxides in high yield; removal of N-Cbz and N-t-Boc groups from protected methionine sulfoxides was also achieved without loss of configuration at sulfur. (C) 1994 Elsevier Science Ltd. All rights reserved.