Synthesis of chiral, amphiphilic, and water-soluble chiral macrocycles via urea formation.

Summary, in English

A simple, efficient, and flexible procedure for the synthesis of chiral, amphiphilic, and water-soluble macrocycles is reported. Acylation of p-xylylenediamine with N-Fmoc-protected glycine, -aspartic acid, -glutamic acid, and -arginine, followed by removal of Fmoc-groups, gave amino acid:p-xylylene conjugate diamines, which were converted to ten macrocycles via stepwise urea formation using p-nitrophenyl chloroformate. -Aspartic acid-containing macrocyles proved to be soluble in aqueous buffers and a macrocycle containing four aspartate residues was found to recognize arginine and arginine esters with moderate affinity.

• Author: T Bhattacharyya; Anders Sundin; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2003
• Language: English
• Pages: 7921-7928
• Publication/Series: Tetrahedron
• Volume: 59
• Issue: 40
• Links: http://dx.doi.org/10.1016/j.tet.2003.08.019
• Document type: Journal article
• Publisher: Elsevier
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 0040-4020