Synthesis and characterization of a derivative of 2-L-N-(L-glutamyl-Lglutaminyl) amino-3-phenylpropan-1-o1 a proposed C-terminal peptide sequence of metabolites of Trichoderma spp.
Abstract
The y-benzyl ester of the 2,4-dinitrophenyl ether of 2-l -N-(l-glutamyl-L-glutaminyl) amino-3-phenylpropan-l-ol, the C-terminal sequence of a number of antibiotic fungal peplides, has been
synthesized. Evidence is presented that rearrangements did not occur at either of the two peptide
bond forming steps. However, 2-l-pyroglutamylamino-3-phenyl-1-(2', 4'-dinitrophenoxy)propane
was always a byproduct in the reaction of the glutamylphenylalaninol ether with r-benzyl N-tbutyloxycarbonylglutamic
acid. The pyranyl ether protecting group of l-2-(N-L-t-butyloxycarbonylglutamyl)
amino-3-phenyl-1-(tetrahydropyranyl-2' -)oxypropane could be selectively hydrolysed with
lithium tetrafluoroborate. On a synthésizé I'ester y-benzyl de I'éther 2,4-binitrophenyl de 2-L -N-(l-glutamyl-L-glutaminyl)
amino-3-phenyl-I-oI, la sequence terminale-C d'un nombre de peptides de mycètes antibiotiques.
Les faits presentés ici démontrent que les réarrangements ont lieu à nulle étape où deux peptides
forment des liaisons. Néanmoins, Ie propane 2-L-pyroglutamylamino-3-phenyl-1-(2',4'-binitro-phenoxyl)
a constitué un dérivé constant de Ia réaction de I'éther glutamylphenylalaninol avec I'acide
y-benzyl N-t-butyloxycarbonylglutamique. On a réussi à hydrolyser, au moyen du telratluoroborate
de lithium, Ie groupe protegeant I'ether pyranyl du propane-L-2-(N-L -t-butyloxycarbonylglutamyl)
amino-3-phenyl-1-oxy(tetrahydropyranyl-2').
Citation
Feicht, A., A.G. Mcinnes, D.G. Smith, A. Taylor, and J.A. Walter. "Synthesis and characterization of a derivative of 2-L-N-(L-glutamyl-Lglutaminyl) amino-3-phenylpropan-1-o1 a proposed C-terminal peptide sequence of metabolites of Trichoderma spp." Proceedings of the Nova Scotian Institute of Science. 39.2 (1991): 67-74. Print.