Synthetic of α-Methylhistidine by Catalytic Phase-Transfer Alkylations
- 1 April 1989
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 19 (7) , 1157-1165
- https://doi.org/10.1080/00397918908054518
Abstract
α-Methylhistidine was prepared by two complementary routes using a catalytic phase-transfer alkylation procedure. Construction of the product was achieved either by alkylation of an alanine Schiff base ester with an imidazole-containing electrophile or by methylation of a protected histidine derivative. Hydrolysis of the protecting groups afforded α-MeHis·2HCl in 27–41% overall yield.Keywords
This publication has 22 references indexed in Scilit:
- The Regiospecific Alkylation of Histidine Side ChainsSynthesis, 1987
- Regiospecific Synthesis of 3-Substituted L-HistidinesSynthesis, 1987
- Induced histidine decarboxylase in endotoxic shock: Identification of the enzyme in rat liver and influence of its inhibitors on survival parametersInflammation Research, 1986
- Importance of amino acids on vasopressin-stimulated water flow.Journal of Clinical Investigation, 1985
- Role of Histamine in Implantation: Inhibition of H istid me Decarboxylase Induces Delayed Implantation in the RabbitBiology of Reproduction, 1981
- Potential histidine decarboxylase inhibitors. 1. .alpha.- and .beta.-Substituted histidine analogsJournal of Medicinal Chemistry, 1977
- Inhibition of histidine decarboxylase. Derivatives of histidineJournal of Medicinal Chemistry, 1977
- An Improved Synthesis of DL-HistidineAgricultural and Biological Chemistry, 1974
- The synthesis of .ALPHA.-methylamino acids.Agricultural and Biological Chemistry, 1974
- NotesJournal of the Chemical Society, 1961