Sugar recognition with a dihydroxyborane derivative layer assembled on gold electrode

Citation
K. Oshima et al., Sugar recognition with a dihydroxyborane derivative layer assembled on gold electrode, NIP KAG KAI, (6), 2000, pp. 405-410
Citations number
31
Language
GIAPPONESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
NIPPON KAGAKU KAISHI
ISSN journal
0369-4577 → ACNP
Issue
6
Year of publication
2000
Pages
405 - 410
Database
ISI
SICI code
0369-4577(200006):6<405:SRWADD>2.0.ZU;2-G
Abstract
Properties of dihydroxy[3-(3-mercaptopropanamido) phenyl]borane (1) in the form of self-assembled monolayer on a gold electrode were studied by quartz crystal microbalance (QCM) method. The monolayer of 1 with surface coverag e of 7.6 x 10(-10) mol/cm(2) aas obtained by immersing the gold electrode i n aqueous solution of 1. The monolayer was found to bind D-fructose reversi bly to form sugar/boran complexes in alkaline media. Selectivity of sugars (association constants K = 100, 4000, congruent to 0 and congruent to 0 M-1 for n-glucose, D-fructose, sucrose and methyl alpha-D-xylopyranoside, resp ectively) was consistent with the previous works concerning homogeneous sol ution of dihydroxyboranes. Although pH dependence of the sugar-binding abil ity of the dihydroxyborane in monolayer resembled that in homogeneous solut ion, the following remarkable characteristics were found for the assembled dihydroxybsrane: (1) The dihydroxyborane in monolayer exhibited a greater p K(a) value than that in homogeneous solution, which was explained by the in teraction between neighboring trihydroxoborates RB(OH)(3)(-). (2) The sugar -binding ability of the assembled dihydroxyborane was noticeably sensitive to pH depending on the square of [trihydroxoboratel]/[dihydroxyborane] rati o.