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Molecular structure and conformation in the crystal of  N -Boc-Met-Cpg-Phe-OMe, a conformationally restricted tripeptide derivative, structurally related to the chemotactic antagonist agent  N -Boc-Met-Leu-Phe-OMe is reported. In the title compound the native central Leu residue has been replaced with the unusual cyclic and achiral quaternary amino acid residue of the 1-aminocyclopent-3-ene-1-carboxylic acid (Cpg). The peptide backbone adopts a type II  β -turn (C 10 ) conformation at the –Met-Cpg- sequence with a distance, between the terminal pseudo-ring atoms O 6  · · · C 3 , of 5.49(1)Å. The tripeptide crystallizes in the monoclinic crystal system, space group  P 2 1 , cell parameter:  a  = 5.867(7) Å,  b  = 23.54(2) Å,  c  = 10.34(1) Å,  β  = 99.74(5)°,  V  = 1407(2) Å 3 ; empirical formula C 26 H 37 N 3 O 6 S; needle crystals were obtained by slow evaporation of an ethyl acetate solution, after 4 days, at room temperature. The low diffraction power of the crystals, it was impossible to obtain crystal structure from normal diffractometer data, suggested to utilize X-ray synchrotron radiation.

zeitschrift für kristallographie

X-ray crystal structure and conformation of  N -( tert -butyloxycarbonyl)-L-methionyl-(1-aminocyclopent-3-ene-1-carbonyl)-L-phenylalanine methyl ester (Boc 0 -Met 1 -Cpg 2 -Phe 3 -OMe)