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

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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.

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Acknowledgements

The authors thank the Department of Science and Technology (DST-SR/SI/OC-69/2008), Department of Biotechnology (DBT: BT/PR16620/NER/95/223/2015), and COE-FAST scheme [5-5/2014-TS.VII], MHRD, New Delhi, Govt. of India for generous funding.

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Correspondence to Subhendu Sekhar Bag.

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Handling editor: R. Hasmukhlal.

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Bag, S.S., De, S. & Bhuyan, S. Intramolecular cyclization of isothiocyanyl amino acids/peptide: arrival at unnatural thioxoimidazolidinyl/thioxooxazolidinyl amino acids. Amino Acids 54, 1451–1459 (2022). https://doi.org/10.1007/s00726-022-03186-w

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  • DOI: https://doi.org/10.1007/s00726-022-03186-w

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