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异硫氰酸基氨基酸/肽的分子内环化:生成非天然硫代咪唑烷基/硫代恶唑烷基氨基酸。

Intramolecular cyclization of isothiocyanyl amino acids/peptide: arrival at unnatural thioxoimidazolidinyl/thioxooxazolidinyl amino acids.

作者信息

Bag Subhendu Sekhar, De Suranjan, Bhuyan Shilpa

机构信息

Chemical Biology/Genomics Laboratory, Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam, 781039, India.

Centre for the Environment, Indian Institute of Technology Guwahati, North Guwahati, Assam, 781039, India.

出版信息

Amino Acids. 2022 Nov;54(11):1451-1459. doi: 10.1007/s00726-022-03186-w. Epub 2022 Jul 23.

Abstract

A novel intramolecular cyclization of isothiocyanyl amino acids/peptide is reported to arrive at unnatural thioxoimidazolidinyl (TOI)/thioxooxazolidinyl (TOO) amino acids for the first time. Interestingly, analogous isothiocyanyl amines under a similar reaction condition either follow 5-endo-dig cyclization to offer 5-membered thiourea or acyclic diethylaminyl thiourea derivative instead of 6-membered cyclic thiourea.

摘要

据报道,一种新型的异硫氰基氨基酸/肽分子内环化反应首次得到了非天然的硫代氧代咪唑烷基(TOI)/硫代氧代恶唑烷基(TOO)氨基酸。有趣的是,类似的异硫氰基胺在类似的反应条件下,要么进行5-内型-亲核环化反应生成五元硫脲,要么生成无环的二乙氨基硫脲衍生物,而不是六元环硫脲。

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