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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
1997-1-27
pubmed:abstractText
Replacement of the alpha-carbon with a nitrogen in alpha-amino acids gives rise to azaamino acids. Most examples of azaamino acids that have been incorporated into peptides are linear analogs, in which conformational effects are restricted to the immediate vicinity of the urea bond. In contrast to the linear azaamino acids, the heterocyclic analogs might be expected to exhibit stronger conformational preferences, but examples of this class of azaamino acids are very limited. We synthesized tetrahydrophthalazine (THPhth) as a constrained phenylalanine analog and elaborated it into the model pseudotripeptide N-¿([N-alanyl]-1,2,3,4-tetrahydro-2-phthalazinyl)carbonyl)¿-L-alan ine (1). As shown by NMR studies, tetrahydrophthalazine 1A has a secondary structure in which psi THphth is fixed at 16-18 degrees and there are two equal populations of cis and trans amide bonds from the N-terminal alanine.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Mar
pubmed:issn
0367-8377
pubmed:author
pubmed:issnType
Print
pubmed:volume
47
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
142-7
pubmed:dateRevised
2000-12-18
pubmed:meshHeading
pubmed:year
1996
pubmed:articleTitle
A pseudopeptide incorporating the tetrahydrophthalazine nucleus, a constrained aza analog of phenylalanine.
pubmed:affiliation
Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, New Jersey, USA.
pubmed:publicationType
Journal Article