Self-Assembling Properties of Peptide Derivatives Composed of Urea Spacer.

Accession number;02A0304376
Title;Self-Assembling Properties of Peptide Derivatives Composed of Urea Spacer.
Author; MORIUCHI TOSHIYUKI (Osaka Univ., Grad. Sch.) TAMURA TAKASHI (Osaka Univ., Grad. Sch.) HIRAO TOSHIKAZU (Osaka Univ., Grad. Sch.)
Journal Title;Abstracts. Symposium on Biofunctional Chemistry
Journal Code:L0836A
ISSN:
VOL.16th;NO.;PAGE.40-41(2001)
Figure&Table&Reference;
Pub. Country;Japan
Language;Japanese
Abstract;Urea tetrapeptide derivatives composed of two dipeptide chains (-L-Ala-L-Pro-NHPy) have been synthesized to form stable hydrogen-bonded duplexes in both solid and solution states, which were investigated by 1H-NMR, FT-IR and X-ray crystallographic analyses. The single-crystal X-ray structure determination of the urea tetrapeptide derivative 1 composed of two -L-Ala-L-Pro-NHPy revealed that two molecules of 1 form a hydrogen-bonded duplex by six intermolecular hydrogen bonds. Proton magnetic resonance nuclear Overhauser effect(NOE) study of 1 indicates the similar hydrogen-bonded duplex even in solution. The urea tetrapeptide derivative composed of two dipeptide chains (-L-Ala-L-Pro-NHCH2Pyr) exhibited both monomer and eximer emissions in the fluorescence spectra, supporting the formation of a duplex structure. Such hydrogen-bonded duplexes were not organized in the case of the urea tetrapeptide derivative composed of two dipeptide chains (-L-Ala-L-Pro-OEt) and the urea dipeptide derivative composed of only one dipeptide chains (-L-Ala-L-Pro-NHCH2Pyr), suggesting that the NH adjacent to the pyridyl moiety in each side and the reasonable sequence of hydrogen-bonding sites are considered to be a crucial factor for the formation of a duplex. (author abst.)