Lübbe C, van Pée K H, Salcher O, Lingens F
Hoppe Seylers Z Physiol Chem. 1983 Apr;364(4):447-53. doi: 10.1515/bchm2.1983.364.1.447.
Pseudomonas pyrrocinia ATCC 15958 and a mutant strain (ACN) of Pseudomonas aureofaciens ATCC 15926 possess a mechanism for the degradation of the tryptophan side chain. Indole, indole-3-carboxylic acid, indole-3-acetic acid and the corresponding compounds chlorinated or brominated at position 7, as well as indole-3-pyruvate and 7-chloroindole-3-pyruvate, were isolated from bacterial cultures. The chlorinated indole derivatives were isolated after the addition of 7-chloro-DL-tryptophan to cultures of P. pyrrocinia whereas their bromo analogues were found in the culture medium of the mutant strain ACN of P. aureofaciens, grown in the presence of sodium bromide. Enzymatic studies show that tryptophan is transaminated to indole-3-pyruvate, which is transformed to indole-3-acetaldehyde. Dehydrogenation of indole-3-acetaldehyde leads to indole-3-acetic acid, which is further metabolized to indole-3-carboxaldehyde, and converted by dehydrogenation to indole-3-carboxylic acid. Indole is formed by the spontaneous decarboxylation of indole-3-carboxylic acid.
吡咯菌素假单胞菌ATCC 15958和金黄色假单胞菌ATCC 15926的突变菌株（ACN）具有降解色氨酸侧链的机制。从细菌培养物中分离出了吲哚、吲哚-3-羧酸、吲哚-3-乙酸以及在7位氯化或溴化的相应化合物，还有吲哚-3-丙酮酸和7-氯吲哚-3-丙酮酸。在向吡咯菌素假单胞菌培养物中添加7-氯-DL-色氨酸后分离出了氯化吲哚衍生物，而在溴化钠存在下生长的金黄色假单胞菌突变菌株ACN的培养基中发现了它们的溴代类似物。酶学研究表明，色氨酸经转氨作用生成吲哚-3-丙酮酸，后者转化为吲哚-3-乙醛。吲哚-3-乙醛脱氢生成吲哚-3-乙酸，吲哚-3-乙酸进一步代谢为吲哚-3-甲醛，并通过脱氢转化为吲哚-3-羧酸。吲哚由吲哚-3-羧酸的自发脱羧反应形成。
