Isothiocyanyl Alanine as a Synthetic Intermediate for the Synthesis of Thioureayl Alanines and Subsequent Aminotetrazolyl Alanines,The Journal of Organic Chemistry

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Isothiocyanyl Alanine as a Synthetic Intermediate for the Synthesis of Thioureayl Alanines and Subsequent Aminotetrazolyl Alanines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-11-03 00:00:00 , DOI: 10.1021/acs.joc.7b02103
Subhendu Sekhar Bag ₁ , Suranjan De ₁

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The synthesis of unnatural amino acids with small side-chain functionalities usable for further transformations is highly demanding for the expansion of the genetic code and other possible biotechnological applications. To this end, we wanted to report the utility of an unexplored unnatural amino acid, isothiocyanyl alanine (^NCSAla = Ita), for the synthesis of another class of unnatural amino acids, thioureayl alanines (^TUAla = Tua). The synthesis of a third class of unnatural amino acids, amino tetrazolyl alanines (^ATzAla = Ata), in a very good yield was subsequently achieved utilizing thioureayl alanines. Thus, a variety of aliphatic- and aromatic-substituted thioureayl alanines and aromatic-substituted amino tetrazolyl alanines were successfully synthesized in good to excellent yields. The photophysical properties of three of the fluorescent unnatural amino acids from two classes were also studied and presented herein.

中文翻译：

异硫氰基丙氨酸作为合成中间体，用于合成硫脲基丙氨酸和随后的氨基四唑基丙氨酸

具有较小侧链功能的非天然氨基酸的合成可用于进一步转化，这对于扩展遗传密码和其他可能的生物技术应用非常需要。为此，我们想报告未开发的非天然氨基酸异硫氰基丙氨酸（^NCS Ala = Ita）在合成另一类非天然氨基酸硫脲基丙氨酸（^TU Ala = Tua）中的实用性。第三类非天然氨基酸氨基四唑基丙氨酸的^合成Ala = Ata），随后利用硫脲基丙氨酸获得了非常高的收率。因此，成功地以良好至优异的产率成功地合成了多种脂族和芳族取代的硫脲基丙氨酸和芳族取代的氨基四唑基丙氨酸。本文还研究并提出了来自两类的三种荧光非天然氨基酸的光物理性质。

更新日期：2017-11-03

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