Solid-state conformation of a hybrid tripeptide between beta-amino acid; 8-aminocyclooct-4-enecarboxylic acid and 2-aminoisobutyric acid.
An eight-membered cyclic beta-amino acid, 8-aminocyclooct-4-enecarboxylic acid, was designed as a conformationally restricted non-proteinogenic amino acid. A hybrid tripeptide containing this eight-membered cyclic beta-amino acid and 2-aminoisobutyric acids was synthesized by conventional solution methods. The conformation of the tripeptide was studied using X-ray analysis and was shown to form an eleven-membered hydrogen-bonded turn (3(11)-helical structure) in the solid state.
Tanaka
M
M
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan. suemune@phar.kyushu-u.ac.jp
Oba
M
M
Ichiki
T
T
Suemune
H
H
D000596:Amino Acids / Q000737:chemistry*; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis*; D000621:Aminoisobutyric Acids / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D008958:Models, Molecular; D009842:Oligopeptides / Q000737:chemistry*; D011487:Protein Conformation
C446965:8-aminocyclooct-4-enecarboxylic acid; D000596:Amino Acids; D000598:Amino Acids, Cyclic; D000621:Aminoisobutyric Acids; D007202:Indicators and Reagents; D009842:Oligopeptides; C100049:2-aminoisobutyric acid