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

Subhendu Sekhar Bag; Suranjan De; Shilpa Bhuyan

doi:10.1007/s00726-022-03186-w

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

Subhendu Sekhar Bag, Suranjan De, Shilpa Bhuyan

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1451-1459
Number of pages	9
Journal	Amino Acids
Volume	54
Issue number	11
DOIs	https://doi.org/10.1007/s00726-022-03186-w
State	Published - Nov 2022
Externally published	Yes

Bibliographical note

Funding Information:
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.

Publisher Copyright:
© 2022, The Author(s), under exclusive licence to Springer-Verlag GmbH Austria, part of Springer Nature.

Keywords

5-endo-dig cyclization
5-membered thiourea
Intramolecular cyclization of isothiocyanyl amino acids/peptide
Isothiocyanyl amines
Unnatural thioxoimidazolidinyl (TOI)/thioxooxazolidinyl (TOO) amino acids

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10.1007/s00726-022-03186-w

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

Abstract

Bibliographical note

Keywords

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