Synthesis of chiral, amphiphilic, and water-soluble chiral macrocycles via urea formation.
Författare
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.
Avdelning/ar
Publiceringsår
2003
Språk
Engelska
Sidor
7921-7928
Publikation/Tidskrift/Serie
Tetrahedron
Volym
59
Issue
40
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Organic Chemistry
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 0040-4020