In:
Chemistry – A European Journal, Wiley, Vol. 11, No. 24 ( 2005-12-09), p. 7315-7321
Abstract:
As part of a drug‐delivery project, we designed and synthesised a novel hydroxylamine cholesterol‐based anchor to ensure the chemoselective ligation of recognition patterns onto multilamellar vesicles by oxime ligation. The entry of a glyoxylyl peptide into the vesicles was unexpectedly assisted by the formation of the α‐oxo oxime bond. We studied extensively the kinetic and thermodynamic aspects of this phenomenon. Briefly, for a glyoxylyl peptide, the speed and ability to enter the vesicle were dependent upon 1) the presence of a hydroxylamine anchor of the type CholE 3 ONH 2 , 2) the amount of peptide engaged in the ligation and 3) the flip‐flop motion permitted by the different formulations, in which the presence of cholesterol seems to play an important role.
Type of Medium:
Online Resource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.200500480
Language:
English
Publisher:
Wiley
Publication Date:
2005
detail.hit.zdb_id:
1478547-X
