title: Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid.
abstract: A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme.
authors.affiliation: Faculty of Agriculture and Lifescience, Hirosaki University, 3-Bunkyo-cho, Hirosaki 036-8561, Japan.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Yamamoto
authors.forename: Naoki
authors.initials: N
authors.lastname: Watanabe
authors.forename: Hiroko
authors.initials: H
authors.lastname: Matsuda
authors.forename: Keiichiro
authors.initials: K
authors.lastname: Oohara
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Araya
authors.forename: Masaru
authors.initials: M
authors.lastname: Hashimoto
authors.forename: Kazuo
authors.initials: K
authors.lastname: Miyairi
authors.forename: Isao
authors.initials: I
authors.lastname: Okazaki
authors.forename: Minoru
authors.initials: M
authors.lastname: Saito
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Shimizu
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Kato
authors.forename: Toshikatsu
authors.initials: T
authors.lastname: Okuno
mesh_terms: D002240:Carbohydrate Sequence; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006603:Hexuronic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D008958:Models, Molecular; D008968:Molecular Conformation; D011096:Polygalacturonase / Q000378:metabolism*; D013379:Substrate Specificity; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D006603:Hexuronic Acids; D013457:Sulfur Compounds; C007819:galacturonic acid; D011096:Polygalacturonase