Linked Life Data

15595666

Source:http://linkedlifedata.com/resource/pubmed/id/15595666

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1-2
pubmed:dateCreated
2004-12-14
pubmed:abstractText
In the course of the synthesis and purification of new polymyxins and analogues, formation of a by-product with identical mass was observed and it was believed that this might be the result of acyl migration from the Nalpha- to the Ngamma-position of residue alpha,-gamma-diaminobutyric acid 1 (Dab1) under acidic conditions. Therefore, a LC-MS/MS study was initiated to establish the stability of polymyxin B3 in aqueous solution at room temperature and 60 degrees C, as well as different pH values (i.e. 1.4, 4.4 and 7.4). It was shown that the by-product, which is actually formed in the course of the purification of polymyxin B3 after evaporation in acidic medium, has a retention time similar to Ngamma-polymyxin B3. Acyl-migration occurred most rapidly at 60 degrees C and pH 7.4. Furthermore, it was established that migration of the acyl from the Nalpha- to the Ngamma-position of residue Dab1 is reversible and that the equilibrium seems to be in favor of the Nalpha-acylated compound.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
0021-9673
pubmed:author
pubmed:issnType
Print
pubmed:day
26
pubmed:volume
1058
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
183-9
pubmed:dateRevised
2009-1-15
pubmed:meshHeading
pubmed:year
2004
pubmed:articleTitle
Liquid chromatography-mass spectrometry study towards the pH and temperature-induced N-acyl migration in polymyxin B.
pubmed:affiliation
Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't