Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid.
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.
Yamamoto
Kazunori
K
Faculty of Agriculture and Lifescience, Hirosaki University, 3-Bunkyo-cho, Hirosaki 036-8561, Japan.
Watanabe
Naoki
N
Matsuda
Hiroko
H
Oohara
Keiichiro
K
Araya
Tomoyuki
T
Hashimoto
Masaru
M
Miyairi
Kazuo
K
Okazaki
Isao
I
Saito
Minoru
M
Shimizu
Tetsuya
T
Kato
Hiroaki
H
Okuno
Toshikatsu
T
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*
D004791:Enzyme Inhibitors; D006603:Hexuronic Acids; D013457:Sulfur Compounds; C007819:galacturonic acid; D011096:Polygalacturonase