TY - JOUR
T1 - Structural Analysis of β-Turn Mimics Containing a Substituted 6-Aminocaproic Acid Linker
AU - Takusagawa, Fusao
AU - Kitagawa, Osamu
AU - Velde, David Vander
AU - Dutta, Dinah
AU - Morton, Martha
AU - Aubé, Jeffrey
PY - 1995/5
Y1 - 1995/5
N2 - A series of β-turn models have been prepared consisting of the dipeptide Ala-Gly cyclized with all stereoisomers of 6-amino-3,5-dimethylcaproic acid and 6-amino-3-methylcaproic acid, as were related peptides based on Gly-Gly and Ala-Ala. The requisite linkers were made using routes featuring stereoselective ring-expansion reactions and the syntheses completed using standard methodology. A preliminary examination of these compounds has been carried out using NMR spectroscopy, circular dichroism, and, in several cases, X-ray crystallography. These studies indicate that, depending on linker stereochemistry, different proportions of type II and type I turns were observed in solution. Both type I and type II turns were observed in the solid state.
AB - A series of β-turn models have been prepared consisting of the dipeptide Ala-Gly cyclized with all stereoisomers of 6-amino-3,5-dimethylcaproic acid and 6-amino-3-methylcaproic acid, as were related peptides based on Gly-Gly and Ala-Ala. The requisite linkers were made using routes featuring stereoselective ring-expansion reactions and the syntheses completed using standard methodology. A preliminary examination of these compounds has been carried out using NMR spectroscopy, circular dichroism, and, in several cases, X-ray crystallography. These studies indicate that, depending on linker stereochemistry, different proportions of type II and type I turns were observed in solution. Both type I and type II turns were observed in the solid state.
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U2 - 10.1021/ja00124a001
DO - 10.1021/ja00124a001
M3 - Article
AN - SCOPUS:0029011697
VL - 117
SP - 5169
EP - 5178
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 19
ER -