Biohydroxylations of Cbz-protected alkyl substituted piperidines by Beauveria bassiana ATCC 7159

Biohydroxylations of Cbz-protected alkyl substituted piperidines by Beauveria bassiana ATCC 7159
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DOI:
10.1039/a805800h
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发表时间:
1998-10-21
期刊:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
影响因子:
--
通讯作者:
Flitsch, SL
Flitsch, SL
中科院分区:
其他
文献类型:
--
作者:
Aitken, SJ;Grogan, G;Flitsch, SL

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当与球孢白僵菌ATCC 7159一起孵育时,N-苄氧羰基(Cbz)保护的哌啶比相应的N-苯甲酰基类似物具有更大的区域选择性被羟基化。Cbz-保护的哌啶1-3,5-7,已经通过生长该真菌的细胞悬浮液进行生物转化,以高达48%的产率主要产生4-羟基化产物。羟基化的区域特异性仅在N-Cbz-3-甲基哌啶3和N-Cbz-2-甲基哌啶4中显著受损,其中羟基化发生在3和4位。
N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with greater regioselectivity than the corresponding N-benzoyl analogues when incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protected piperidines 1-3, 5-7, have been biotransformed by growing cell suspensions of this fungus to yield predominantly 4-hydroxylated products in up to 48% yield. The regiospecificity of hydroxylation was only compromised significantly with N-Cbz-3-methylpiperidine 3 and N-Cbz-2-methylpiperidine 4 where hydroxylation occurred in both the 3 and 4 positions.