Synthesis of chiral, amphiphilic, and water-soluble chiral macrocycles via urea formation.
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/127907
- author
- Bhattacharyya, T ; Sundin, Anders LU and Nilsson, Ulf LU
- organization
- publishing date
- 2003
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 55e5e7b5-7691-4651-8d8b-f15ee6c9c4f9 (old id 127907)
- date added to LUP
- 2016-04-01 17:13:19
- date last changed
- 2022-01-29 01:11:47
@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}}, doi = {{10.1016/j.tet.2003.08.019}}, volume = {{59}}, year = {{2003}}, }