Tryptophane Metabolism

The Isolation and Synthesis of the Naturally Occurring a-Amino Acids.

“…(f) By condensation with acetylglycine Herbst and Shemin (159) used acetylglycine rather than benzoylglycine (hippuric acid) for the synthesis of phenylalanine. Baugess and Berg (26) prepared indolepyruvic acid by the azlactone method and then made the amino acid by reduction of the oxime. The indolealdehyde was prepared from indole by Majima and Kotake's method (217).…”

Preparation and Properties of β-3-Indolyl Compounds Related to Tryptophan Metabolism1

“…The reduction of I to V in 85% yield by hydrogenation over Raney nickel was indicated without details in an earlier report. 22 The preparation of V in two steps from gramme and diethyl acetoxymalonate (52% overall yield) was reported recently from this laboratory.23 A circuitous reduction of methyl indolepyruvate with sodium borohydride also has been described.11 The earliest synthesis of V involved basic racemization of the D-antipode21 which was obtained by fermentation of L-tryptophan with Oidium lactis.2* V is stable in crystalline form, or in organic solutions. Decomposition occurs when aqueous solutions are concentrated,24 however, and is accelerated by mineral acids.…”

Struktur und Biosynthese von Collinolacton aus Streptomyces sp. und Beiträge zum Screening neuer Wirkstoffe

“…Indol-3-milchsäure (111) wurde als erstes 1911 von F. EHRLICH und K. JACOBSEN beschrieben, die feststellten, dass die Verbindung aus Tryptophan gebildet wird, das durch eine Hefe (Oidium lactis) verdaut wird. [183,184] Für 111 ist eine antifungische Aktivität gegen Candida albicans [179] beschrieben, die in Plattendiffusionstests nicht nachgewiesen werden konnte.…”