Tailor‐Made Amino Acids in Pharmaceutical Industry: Synthetic Approaches to Aza‐Tryptophan Derivatives. Issue 70 (25th October 2021)

• Record Type: Journal Article
• Authors: Han, Jianlin; Lyutenko, Nataliya V.; Sorochinsky, Alexander E.; Okawara, Ayaka; Konno, Hiroyuki; White, Sarah; Soloshonok, Vadim A.
• Is Part Of: Chemistry. Volume 27:Issue 70(2021)
• Page Start: 17510
• Page End: 17528
• Publication Date: 2021-10-25
• Subjects: amino acids -- antimetabolites -- asymmetric synthesis -- chemical structural mimicry -- luminescent bio-markers -- peptides -- pharmaceutical drugs; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202102485
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Over the recent years there has been a noticeable upsurge of interest in aza‐analogs of tryptophan which are isosteric to the latter and found numerous applications in medicinal, bioorganic chemistry, and peptide research. In the present review article, five aza‐tryptophan derivatives are profiled, including aza‐substitution in the positions 2, on the five‐membered ring, as well as in positions 4, 5, 6, and 7 on the six‐membered ring. A detailed and comprehensive literature overview of the synthetic methods for the preparation of these aza‐tryptophans is presented and general facets of the biological properties and most promising applications are discussed. Abstract : This review profiles five tailor‐made amino acids, aza‐tryptophan derivatives, which include aza‐substitution in positions 2, 4, 5, 6, and 7 on the aromatic rings of tryptophan. The synthesis, medicinal chemistry and biological properties, and most promising applications of these aza‐tryptophan are discussed.