Bend ribbon-forming tetrahydrofuran amino acids.
Short oligomeric chains of C-glycosyl beta-D-arabinofuranose configured tetrahydrofuran amino acids (where the C-2 and C-5 substituents of the tetrahydrofuran ring are cis to each other) exhibit a well-defined repeating turn secondary structure stabilised by (i, i - 2) inter-residue hydrogen bonds. This is in contrast to the epimeric alpha-D-arabinofuranose oligomer (where the C-2 and C-5 substituents of the tetrahydrofuran ring are trans to each other) in which there is no indication of any secondary structure in solution.
Smith
Martin D
MD
Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY.
Claridge
Timothy D W
TD
Sansom
Mark S P
MS
Fleet
George W J
GW
D000596:Amino Acids / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D000596:Amino Acids; D005663:Furans; C018674:tetrahydrofuran