Linked Life Data

2092933

Source:http://linkedlifedata.com/resource/pubmed/id/2092933

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
12
pubmed:dateCreated
1991-6-14
pubmed:abstractText
Three novel lipid A analogs, which have an alpha- or beta-glycosidically bound phosphonooxyethyl group instead of the alpha-glycosyl phosphate group of natural lipid A, were synthesized. The first analog (2) had an alpha-phosphonooxyethyl group on the identical acylated disaccharide 4'-phosphate structure found in natural lipid A (from Escherichia coli) and hence differed from the latter only in the nature of the acidic group at position 1. The second one (3) had tetradecanoyl groups in place of the two (R)-3-hydroxytetradecanoyl groups bound to the 2- and 3-hydroxyl function of 2, retaining the alpha-phosphonooxyethyl group. The structure of the third analog (4) was the same as that of 3 except that the phosphonooxyethyl group of the former was beta-oriented. Compounds 2 and 3 exhibited potent activity against Meth A at the same level as natural lipid A, whereas 4 showed less activity. This fact revealed that the glycosidic phosphate is not a prerequisite for the antitumor activity of lipopolysaccharide. It can be replaced with a phosphonooxyethyl group without any loss of activity provided that the alpha-anomeric configuration at C-1 is retained. The replacement of the hydroxytetradecanoyl groups with tetradecanoyl groups does not change the activity either.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Dec
pubmed:issn
0009-2363
pubmed:author
pubmed:issnType
Print
pubmed:volume
38
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
3366-72
pubmed:dateRevised
2003-11-14
pubmed:meshHeading
pubmed:year
1990
pubmed:articleTitle
Synthesis and antitumor activity of lipid A analogs having a phosphonooxyethyl group with alpha- or beta-configuration at position 1.
pubmed:affiliation
Research Institute, Daiichi Pharmaceutical Co., Ltd., Tokyo, Japan.
pubmed:publicationType
Journal Article