Multi-purpose synthetic alpha-amino acid featuring coumarin and ureidopyrimidinone motifs on its backbone: Synthesis and peptide formation

TitleMulti-purpose synthetic alpha-amino acid featuring coumarin and ureidopyrimidinone motifs on its backbone: Synthesis and peptide formation
Publication TypeJournal Article
Year of Publication2022
AuthorsRashid, PP, Sanjayan, GJ
JournalTetrahedron Letters
Volume93
Pagination153695
Date PublishedMAR
Type of ArticleArticle
ISSN0040-4039
KeywordsFluorescent amino acids, Fluorescent Peptides, Quadruple hydrogen bonding, Unnatural amino acids, Ureidopyrimidinone
Abstract

Herein we report a synthetic a-amino acid featuring intensely fluorescent coumarin moiety and a strongly self-assembling ureidopyrimidinone (UPy) motif. This two-in-one synthetic amino acid, displaying both fluorescence and self-assembling property, has been synthesized in four easy steps starting from commercially available inexpensive starting materials. Suitably protected amino acid has been incorporated into various peptide sequences, following solution-phase peptide coupling protocols, to demonstrate its synthetic feasibility.(c) 2022 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2022.153695
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.032

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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