Nuclear magnetic resonance study on solvent dependence of side chain conformations of tyrosine and tryptophan derivatives was written by Kobayashi, Junichi;Higashijima, Tsutomu;Sekido, Sachiko;Miyazawa, Tatsuo. And the article was included in International Journal of Peptide & Protein Research in 1981.Category: indole-building-block This article mentions the following:
The stereoselectively 尾-deuterated species of Ac-X-NHMe, Ac-X-OH, and Ac-X-OEt (X = Tyr, Trp) and H-Trp-NHMe were synthesized. 270-MHz 1H NMR spectra of the normal and deuterated species of these aromatic amino acid derivatives were analyzed. For most of the tyrosine and tryptophan derivatives in various polar and nonpolar solvents, the lower-field and higher-field 尾-proton signals were due to the pro-S and pro-R protons, resp. However, the alternative assignments apply for H-Trp-NHMe in aqueous solution and for Ac-Tyr-NHMe and Ac-Trp-NHMe in nonpolar solvents. Such alternative assignments of 尾-proton signals were also found for H-Phe-NHMe, Ac-Phe-NMe2, and Ac-Phe-OtBu. From the analyses of the 1H NMR spectra of tyrosine and tryptophan derivatives, the vicinal coupling constants and rotamer populations about the C伪-C尾 bond were determined in various solvents. The rotamer populations of H-Trp-NHMe, Ac-X-NHMe, Ac-X-OH and Ac-X-OEt depend significantly on solvent polarity. Each of these four types of derivatives exhibits specific solvent-polarity dependences of rotamer populations which were substantially reduced on replacement of 伪-carbonyl group by a methylene group, suggesting the effect of this carbonyl group in the solvent dependence of rotamer populations. In the experiment, the researchers used many compounds, for example, Ethyl acetyl-L-tryptophanate (cas: 2382-80-1Category: indole-building-block).
Ethyl acetyl-L-tryptophanate (cas: 2382-80-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Category: indole-building-block
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles