Synthesis and structural analysis of 6-aminobicyclo[2.2.1]heptane-2-carboxylic acid as a conformationally constrained gamma-turn mimic.
An efficient asymmetric synthesis of 6-aminobicyclo[2.2.1]heptane-2-carboxylic acid as a novel gamma-turn mimic has been achieved. Structural analysis of the gamma-amino acid derivative was carried out using (1)H NMR spectroscopy and intramolecular hydrogen bonding between side chain amides confirmed the turn structure, which had been predicted by Ab initio computational study.
Park
Jin-Seong
JS
Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul, 151-747, South Korea.
Kim
Kyoung Rak
KR
Nam
Hye Young
HY
Yeom
Chang-Eun
CE
Chough
Chieyeon
C
Kwon
Soon Ho
SH
Ro
Seonggu
S
Shin
Dong-Kyu
DK
Kim
B Moon
BM
D000598:Amino Acids, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D009636:Norbornanes; D017433:Protein Structure, Secondary
C533951:6-aminobicyclo(2.2.1)heptane-2-carboxylic acid; D000598:Amino Acids, Cyclic; D001643:Bridged Bicyclo Compounds; D006536:Heptanes; D009636:Norbornanes