Crystal structures of the even and odd bolaform amino acid derivatives (11-N-[benzyloxycarbonyl-L-alanyl]aminoundecanoyl)-L-alanyl benzyl ester and (12-N-[benzyloxycarbonyl-L-alanyl]aminododecanoyl)-L-alanyl benzyl ester.
Reaction of two alpha, omega-aminocarboxylic acids with N- and C-protected alanine leads to bolaform compounds with two secondary amide groups on one end and one such group at the other end. Unsymmetric sheet-like structures are formed in the crystals. (11-N-[Benzyloxycarbonyl-L-alanyl] aminoundecanoyl)-L-alanyl benzyl ester (1) and (12-N-[benzyloxycarbonyl-L-alanyl] aminododecanoyl)-L-alanyl benzyl ester (2) form triclinic crystals (spacegroup P1, No.1) with a = 4.917, b = 5.614, c = 29.02 A. alpha = 88.40, beta = 93.50, gamma = 100.21 degrees, Z = 1 (1) and a = 4.954, b = 5.613, c = 30.23 A, alpha = 93.44, beta = 90.07, gamma = 104.15 degrees, Z = 1 (2). The crystal structures were solved via direct methods and refined to R = 0.040 (1) and 0.078 (2) from 2441 and 2725 reflections.
Schade
B
B
Institute for Organic Chemistry, Freie Universität Berlin, Germany.
Hubert
V
V
André
C
C
Luger
P
P
Fuhrhop
J H
JH
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray / Q000379:methods; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D011336:Probability; D011487:Protein Conformation
C106802:(11-N-(benzyloxycarbonyl-alanyl)aminoundecanoyl)alanyl benzyl ester; C106803:(12-N-(benzyloxycarbonyl-alanyl)aminododecanoyl)alanyl benzyl ester; D004151:Dipeptides; D000409:Alanine