‘Naked-eye’ enantioselective chemosensors for N-protected amino acid anions bearing thiourea units

✍ Scribed by Guangyan Qing; Taolei Sun; Zhihong Chen; Xi Yang; Xiaojun Wu; Yongbing He

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 437 KB
• Volume: 21
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20593

✦ Synopsis

Abstract

Four linear thiourea anion receptors (1–3) derived from simple amino acid have been synthesized and their bonding properties with various chiral N‐protected amino acid anions were examined by using UV–vis and fluorescence titration experiments. Receptors 1a, 2, and 3 exhibit excellent enantioselective recognition abilities towards N‐Boc‐protected alanine anion in the UV–vis spectra, obvious difference in the color of solution indicate that the enantiomers of N‐Boc‐alanine anion could be distinguished by naked eye directly. Receptor 1a is also found to carry out enantioselective fluorescent recognition of the N‐acetyl‐glutamate. ^1^H NMR experiments suggest that hydrogen‐bonding interaction between the host and guest is the main factor in the recognition process. Chirality, 2009 © 2008 Wiley‐Liss, Inc.