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

Bhattacharyya, T; Sundin, Anders LU and Nilsson, Ulf LU (2003) In Tetrahedron 59(40). p.7921-7928
Abstract
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.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
59
issue
40
pages
7921 - 7928
publisher
Elsevier
external identifiers
  • wos:000185585800010
  • scopus:0141852279
ISSN
0040-4020
DOI
10.1016/j.tet.2003.08.019
language
English
LU publication?
yes
id
55e5e7b5-7691-4651-8d8b-f15ee6c9c4f9 (old id 127907)
date added to LUP
2007-07-10 09:14:24
date last changed
2018-05-29 09:32:43
@article{55e5e7b5-7691-4651-8d8b-f15ee6c9c4f9,
  abstract     = {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       = {Bhattacharyya, T and Sundin, Anders and Nilsson, Ulf},
  issn         = {0040-4020},
  language     = {eng},
  number       = {40},
  pages        = {7921--7928},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Synthesis of chiral, amphiphilic, and water-soluble chiral macrocycles via urea formation.},
  url          = {http://dx.doi.org/10.1016/j.tet.2003.08.019},
  volume       = {59},
  year         = {2003},
}