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Biochemistry

Title:		"Biological activity and conformational isomerism in position 9 analogues of the des-1-tryptophan,3-beta-cyclohexylalanine-alpha-factor from Saccharomyces cerevisiae"
Author(s):		Shenbagamurthi P; Kundu B; Raths S; Becker JM; Naider F;
Address:
Journal Title:		Biochemistry
Year:		1985
Volume:		24
Issue:		25
Page Number:		7070 - 7076
DOI:		10.1021/bi00346a008
ISSN/ISBN:		0006-2960 (Print) 0006-2960 (Linking)
Abstract:		"Analogues of the des-1-tryptophan,3-beta-cyclohexylalanine-alpha-factor of Saccharomyces cerevisiae, where the glycyl residue of position 9 was replaced by D-Ala, L-Ala, D-Leu, and L-Leu, were synthesized and evaluated by morphogenesis assays and circular dichroism spectroscopy. Synthesis was accomplished in solution phase with mixed anhydrides and p-nitrophenyl active esters as the coupling agents. All crude dodecapeptides were purified to greater than 98% homogeneity by preparative high-performance liquid chromatography on a reversed-phase column. The Gly9, D-Ala9, and D-Leu9 analogues elicited morphogenic alterations in MATa strains of S. cerevisiae at concentrations of 1-2 micrograms/mL and exhibited similar CD patterns in both trifluoroethanol and tris(hydroxymethyl)aminomethane buffer, pH 7.4. In contrast, the L-Ala9 and L-Leu9 analogues were more than 200 times less active in the morphogenesis assay and had markedly different CD spectra. These results demonstrate that the position 9 residue plays an important role in determining the biological activity and solution conformation of alpha-factor. We suggest the presence of a type II beta-turn in the Lys7-Gln10 region when the alpha-factor assumes its biologically active conformation"
Keywords:		"Alanine/*analogs & derivatives/chemical synthesis/pharmacology Chromatography, High Pressure Liquid Circular Dichroism Indicators and Reagents Magnetic Resonance Spectroscopy Mating Factor Morphogenesis Optical Rotation Peptides/*chemical synthesis/pharma;"
Notes:		"MedlineShenbagamurthi, P Kundu, B Raths, S Becker, J M Naider, F eng GM 20086/GM/NIGMS NIH HHS/ GM 20087/GM/NIGMS NIH HHS/ Comparative Study Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. 1985/12/03 Biochemistry. 1985 Dec 3; 24(25):7070-6. doi: 10.1021/bi00346a008"