Literature DB >> 35870054

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

Subhendu Sekhar Bag1,2, Suranjan De3, Shilpa Bhuyan4.   

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

Entities:  

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

Year:  2022        PMID： 35870054     DOI： 10.1007/s00726-022-03186-w

Source DB:  PubMed          Journal:  Amino Acids        ISSN： 0939-4451            Impact factor:   3.789


  12 in total

1.  Thioamides as useful synthons in the synthesis of heterocycles.

Authors:  Tadeusz S Jagodziński
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

Review 2.  Electrophiles in foods: the current status of isothiocyanates and their chemical biology.

Authors:  Yoshimasa Nakamura; Noriyuki Miyoshi
Journal:  Biosci Biotechnol Biochem       Date:  2010-02-07       Impact factor: 2.043

3.  A protein sequenator.

Authors:  P Edman; G Begg
Journal:  Eur J Biochem       Date:  1967-03

4.  Isothiocyanyl Alanine as a Synthetic Intermediate for the Synthesis of Thioureayl Alanines and Subsequent Aminotetrazolyl Alanines.

Authors:  Subhendu Sekhar Bag; Suranjan De
Journal:  J Org Chem       Date:  2017-11-03       Impact factor: 4.354

5.  Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me4N)SCF3.

Authors:  Thomas Scattolin; Alexander Klein; Franziska Schoenebeck
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

6.  Asparagine and glutamine differ in their propensities to form specific side chain-backbone hydrogen bonded motifs in proteins.

Authors:  Prema G Vasudev; Mousumi Banerjee; C Ramakrishnan; P Balaram
Journal:  Proteins       Date:  2012-01-07

7.  Palladium-Catalyzed Decarboxylative ortho-Amidation of Indole-3-carboxylic Acids with Isothiocyanates Using Carboxyl as a Deciduous Directing Group.

Authors:  R N Prasad Tulichala; Mallepalli Shankar; K C Kumara Swamy
Journal:  J Org Chem       Date:  2018-03-30       Impact factor: 4.354

8.  Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides.

Authors:  Subhendu Sekhar Bag; Suranjan De
Journal:  Bioorg Med Chem Lett       Date:  2018-02-12       Impact factor: 2.823

9.  Carbonic anhydrase inhibitors: the first on-resin screening of a 4-sulfamoylphenylthiourea library.

Authors:  Alessio Innocenti; Angela Casini; Maria C Alcaro; Anna M Papini; Andrea Scozzafava; Claudiu T Supuran
Journal:  J Med Chem       Date:  2004-10-07       Impact factor: 7.446

10.  Tertiary alkylamines as nucleophiles in substitution reactions at heteroaromatic halide during the synthesis of the highly potent pirinixic acid derivative 2-(4-chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylthio)octanoic acid (YS-121).

Authors:  Matthias Gabler; Manfred Schubert-Zsilavecz
Journal:  Molecules       Date:  2011-12-05       Impact factor: 4.411
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