链霉菌菌株对α-紫罗兰酮的立体和区域选择性羟基化作用。
Stereo- and regioselective hydroxylation of alpha-ionone by Streptomyces strains.
作者信息
Lutz-Wahl S, Fischer P, Schmidt-Dannert C, Wohlleben W, Hauer B, Schmid R D
机构信息
Institut für Technische Biochemie, Universität Stuttgart, Stuttgart, Germany.
出版信息
Appl Environ Microbiol. 1998 Oct;64(10):3878-81. doi: 10.1128/AEM.64.10.3878-3881.1998.
A total of 215 Streptomyces strains were screened for their capacity to regio- and stereoselectively hydroxylate beta- and/or alpha-ionone to the respective 3-hydroxy derivatives. With beta-ionone as the substrate, 15 strains showed little conversion to 4-hydroxy- and none showed conversion to the 3-hydroxy product as desired. Among these 15 Streptomyces strains, S. fradiae Tü 27, S. arenae Tü 495, S. griseus ATCC 13273, S. violaceoniger Tü 38, and S. antibioticus Tü 4 and Tü 46 converted alpha-ionone to 3-hydroxy-alpha-ionone with significantly higher hydroxylation activity compared to that of beta-ionone. Hydroxylation of racemic alpha-ionone [(6R)-(-)/(6S)-(+)] resulted in the exclusive formation of only the two enantiomers (3R,6R)- and (3S, 6S)-hydroxy-alpha-ionone. Thus, the enzymatic hydroxylation of alpha-ionone by the Streptomyces strains tested proceeds with both high regio- and stereoselectivity.
总共筛选了215株链霉菌菌株，以检测它们将β-紫罗兰酮和/或α-紫罗兰酮区域选择性和立体选择性羟基化为相应3-羟基衍生物的能力。以β-紫罗兰酮为底物时，15株菌株几乎没有转化为4-羟基产物，且没有一株按要求转化为3-羟基产物。在这15株链霉菌菌株中，弗氏链霉菌Tü 27、沙雷链霉菌Tü 495、灰色链霉菌ATCC 13273、紫色产色链霉菌Tü 38以及抗生链霉菌Tü 4和Tü 46将α-紫罗兰酮转化为3-羟基-α-紫罗兰酮，其羟基化活性比β-紫罗兰酮显著更高。外消旋α-紫罗兰酮[(6R)-(-)/(6S)-(+)]的羟基化仅产生两种对映体(3R,6R)-和(3S,6S)-羟基-α-紫罗兰酮。因此，所测试的链霉菌菌株对α-紫罗兰酮的酶促羟基化反应具有高度的区域选择性和立体选择性。
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