Ethyl 2-[N-(tert-butyloxycarbonyl)-L-alanylamino]-4-methyl-1, 3-thiazole-5-carboxylate reveals a trans orientation of the preceding amide N--H with respect to the thiazole-ring sulfur.
The title molecule, C(15)H(23)N(3)O(5)S, was prepared as a synthetic precursor to 4-methylthiazole-based DNA minor groove binders which would bear chiral amino acids in the sequence. The crystallographic evidence presented herein shows that the aromatic amide NH group preceding the thiazole ring points away from the direction of sulfur. The molecule is biplanar, with the dihedral angle between the N-terminus peptide moiety and the thiazole-containing plane being 49.7 (5) degrees, with a bend at the Calpha carbon.
Singh
U P
UP
Department of Physics, Indian Institute of Science, Bangalore 560 012, India.
Thomas
M
M
Seshadri
T P
TP
Bhattacharya
S
S
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013844:Thiazoles / Q000737:chemistry*
D013844:Thiazoles; C420704:ethyl 2-(N-(tert-butyloxycarbonyl)alanylamino)-4-methyl-1,3-thiazole-5-carboxylate; D004247:DNA; D000409:Alanine