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Int J Pept Protein Res

Title:		Synthesis of alpha-factor analogues containing photoactivatable and labeling groups
Author(s):		Jiang Y; Breslav M; Khare RK; McKinney A; Becker JM; Naider F;
Address:		"Department of Chemistry, College of Staten Island, City University of New York, USA"
Journal Title:		Int J Pept Protein Res
Year:		1995
Volume:		45
Issue:		2
Page Number:		106 - 115
DOI:		10.1111/j.1399-3011.1995.tb01028.x
ISSN/ISBN:		0367-8377 (Print) 0367-8377 (Linking)
Abstract:		"Analogues of alpha-factor, Saccharomyces cerevisiae tridecapeptide mating pheromone (H-Trp-His-Trp-Leu-Gln-Leu-Lys-Pro-Gly-Gln-Pro-Met-Tyr-OH), containing both p-benzoyl phenylalanine (Bpa), a photoactivatable group, and 3-(mono- or di-iodo-4-hydroxyphenyl)propanoic acid (iodinated HPP) or biotin as a tag, were synthesized using solid-phase methodologies on a [phenylacetamido]-methyl (PAM) resin. Bpa was introduced into the peptides using Bpa-hydroxybenzotriazole active ester during peptide chain assembly. Biotinylated alpha-factor analogues were prepared by assembling the desired peptide on the resin, and then reacting a specific amino group either with the symmetrical anhydride of biotin or with biotin using BOP as the activating agent prior to anhydrous hydrogen fluoride cleavage. Iodinated HPP was incorporated by acylating free peptides with Bolton-Hunter reagent (3-[diiodo-4-hydroxyphenyl]propanoic acid hydroxysuccinimide ester) in N,N-dimethylformamide and borate buffer (pH 8.0) solutions. Purification of all peptides to 98% or greater homogeneity was accomplished by high-performance liquid chromatography on a reversed-phase mu-Bondapak C18 column with acetonitrile/water/trifluoroacetic acid as the mobile phase. All products were characterized by amino acid analysis and fast atom bombardment mass spectrometry. Two analogues, alpha-(diiodotyrosine)-His-Bpa-Leu-Gln-Leu-Arg-Pro-Gly-Gln-Pro-Nle-Tyr-O H, and epsilon-(diiodo-HPP)-Lys-His-Bpa-Leu-Gln-Leu-Arg-Pro-Gly-Gln-Pro-Nle-Tyr -OH, were one twentieth to one-fortieth as active as a alpha-factor, and exhibited approximately one order of magnitude lower affinity to the alpha-factor receptor. The results suggest that these two analogues are alpha-factor agonists and that they can be used as probes of the alpha-factor receptor"
Keywords:		"Amino Acid Sequence Binding Sites Biotin/analysis/chemistry Chromatography, High Pressure Liquid Light Mating Factor Molecular Sequence Data Peptides/*chemical synthesis/chemistry/metabolism/pharmacology Phenylalanine/analogs & derivatives/analysis/chemis;"
Notes:		"MedlineJiang, Y Breslav, M Khare, R K McKinney, A Becker, J M Naider, F eng GM 22086/GM/NIGMS NIH HHS/ GM 22087/GM/NIGMS NIH HHS/ Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. Denmark 1995/02/01 Int J Pept Protein Res. 1995 Feb; 45(2):106-15. doi: 10.1111/j.1399-3011.1995.tb01028.x"