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Arch Biochem Biophys

Title:		Chemo-enzymatic synthesis of the glycosylated alpha-mating factor of Saccharomyces cerevisiae and analysis of its biological activity
Author(s):		Saskiawan I; Mizuno M; Inazu T; Haneda K; Harashima S; Kumagai H; Yamamoto K;
Address:		"Graduate School of Biostudies, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto, Japan. iwan@lif.kyoto-u.ac.jp"
Journal Title:		Arch Biochem Biophys
Year:		2002
Volume:		406
Issue:		1
Page Number:		127 - 134
DOI:		10.1016/s0003-9861(02)00416-2
ISSN/ISBN:		0003-9861 (Print) 0003-9861 (Linking)
Abstract:		"The effect of glycosylation on a bioactive peptide was studied using yeast Saccharomyces cerevisiae alpha-mating factor, which is composed of 13 amino acids. In this study, we prepared glycosylated alpha-mating factor by chemo-enzymatic synthesis. At first, N-acetylglucosaminyl alpha-mating factor (Trp-His-Trp-Leu-Gln(GlcNAc)-Leu-Lys-Pro-Gly-Gln-Pro-Met-Tyr) was chemically synthesized by the solid-phase method. Then, using the transglycosylation activity of Mucor hiemalis endo-beta-N-acetylglucosaminidase, we synthesized glycosylated alpha-mating factor with a glutamine-linked sialo complex type oligosaccharide. The biological activity of alpha-mating factor derivatives was examined by means of a growth arrest assay using secreted-protease-defective a cells of S. cerevisiae. The results showed that the bioactivity of glycosylated alpha-mating factor was lower than that of native alpha-mating factor. However, when sialic acid was removed from the complex type sugar chain of glycosylated alpha-mating factor, its bioactivity was recovered. Glycosylated alpha-mating factor exhibited higher resistance against proteolysis than native alpha-mating factor. It was found that the bioactivity of N-acetylglucosaminyl alpha-mating factor was higher than that of alpha-mating factor. Circular dichroism studies indicated that a slight change in the structure of alpha-mating factor may influence its activity"
Keywords:		Acetylglucosamine/*metabolism Agglutinins/biosynthesis Amino Acid Sequence Circular Dichroism Glycoside Hydrolases/metabolism *Glycosylation Mating Factor Mucor/metabolism Peptides/*chemical synthesis/chemistry/*metabolism Protein Conformation Saccharomyc;
Notes:		"MedlineSaskiawan, Iwan Mizuno, Mamoru Inazu, Toshiyuki Haneda, Katsuji Harashima, Satoshi Kumagai, Hidehiko Yamamoto, Kenji eng Research Support, Non-U.S. Gov't 2002/09/18 Arch Biochem Biophys. 2002 Oct 1; 406(1):127-34. doi: 10.1016/s0003-9861(02)00416-2"