ON THE FORMATION OF 3-PHENYLPROPIONATE AND THE DIFFERENT STEREOCHEMICAL COURSE OF THE REDUCTION OF CINNAMATE BY CLOSTRIDIUM-SPOROGENES AND PEPTOSTREPTOCOCCUS-ANAEROBIUS
ON THE FORMATION OF 3-PHENYLPROPIONATE AND THE DIFFERENT STEREOCHEMICAL COURSE OF THE REDUCTION OF CINNAMATE BY CLOSTRIDIUM-SPOROGENES AND PEPTOSTREPTOCOCCUS-ANAEROBIUS
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DOI：
10.1016/0014-5793(81)80030-0
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发表时间：
1981-01-01
期刊：
影响因子：
3.5
通讯作者：
SIMON, H
中科院分区：
文献类型：
--
作者：
GIESEL, H;MACHACEK, G;SIMON, H
根据文献，3-苯基丙酸、4-甲基戊酸、2-甲基丙酸、2-或3-甲基丁酸等是许多不同的蛋白水解和氨基酸发酵梭菌的产物[1 -3]。4-戊酸甲酯和其他挥发性酸也是丙酸杆菌[4]或消化链球菌[5]的产物。令人惊讶的是，导致这些产物的途径和酶是未知的。我们描述了烯酸还原酶，一种结合的Fe-S黄素蛋白，其在NADH依赖性反应中还原非活化的β-不饱和羧酸[6]。来源是C。La 1是在（E）-2-丁烯酸盐上生长的非蛋白水解梭菌。我们在C中发现了相同类型的酶。kluyveri和蛋白水解C.产孢菌然而，它们的底物特异性相当不同[7]。在我们对氨基酸发酵梭菌中烯酸还原酶的发生和生理作用的研究中，我们提出了一个氧化和还原分支来解释上述产物[7]。我们比较了C.产孢链霉菌以及厌氧消化链霉菌将L-苯丙氨酸、（2 R）-苯乳酸、苯丙酮酸和肉桂酸转化为3-苯丙酸。然而，这些过程似乎与C.产孢假单胞菌和厌氧假单胞菌的差异。另外两种立体特异性氘代3-苯基丙酸酯的制备是另外的结果。
According to the literature 3-phenylpropionate, 4-methylpentanoate, 2_methylpropionate, 2-or 3-methylbutyrate and others are products of many different proteolytic and amino acid fermenting clostridia [l-3]. 4-Methylpentanoate and other volatile acids are also products of propionibacteria [4] or peptostreptococci [5]. Surprisingly the route and the enzymes leading to these products are not known. We described enoate reductase a conjugated Fe-S flavoprotein which reduces nonactivated (II, P-unsaturated carboxylates in a NADH-dependent reaction [6]. The source was C. La 1 a non-proteolytic clostridium grown on (E)-2-butenoate. We found the same type of enzyme in C. kluyveri and the proteolytic C. sporogenes. However, their substrate specificity was rather different [7]. Duringour studies on the occurrence and physiological role of enoate reductases in amino acid fermenting clostridia we suggested an oxidative and a reductive branch to explain the above-mentioned products [7]. We compared the capability of resting cells of C. sporogenes as well as Peptostreptococcus anaerobius to convert L-phenylalanine,(2R)-phenyllactate, phenylpyruvate and cinnamate to 3-phenylpropionate. Nevertheless, the processes seem to be so similiar the sterical course of the reduction of (E) cinnamate to 3-phenylpropionate by C. sporogenes and P. anaerobius is different. The preparation of two further stereospecifically deuterated 3-phenylpropionates is an additional result.