Synthesis of sugar-substituted poly(phenylenevinylene)s.
Sugar-containing PPVs, poly{2-[O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)]-5-methoxy-p-phenylenevinylene-alt-p-phenylenevinylene} (PPV-GlcNAc) and poly{2,5-bis-[O-(beta-d-glucopyranosyl)]-p-phenylenevinylene-alt-p-phenylenevinylene} (PPV-Glc(2)), were synthesized via Heck reaction of p-divinylbenzene (DVB) with O-glycosylated hydroquinones, 2,5-dibromo-4-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside (3) and 1,4-bis(O-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2,5-dibromobenzene (6), respectively. Acetyl protecting groups of the PPVs are completely removable under mild conditions (yield 69-87%). The structures were confirmed using (1)H NMR and IR spectra. Size exclusion chromatography (SEC) (eluent: DMF, polystyrene standards) measurements indicated that respective M(n) and M(w)/M(n) values of the obtained polymers are 4.49 x 10(3) and 2.3(5) (PPV-GlcNAc) and 3.86 x 10(3) and 1.3(9) (PPV-Glc(2)). These sugar-containing PPVs are soluble in water/DMF (8/2, v/v) and are recognized by Concanavalin A (Con A), D-glucose-binding protein. Blue shift of lambda(max) of the conjugated polymer backbone was confirmed when the glucose-substituted PPV interacts with Con A. Based on those binding properties, these results revealed that the obtained PPVs with pendant sugars have capabilities for detection of biological stimuli.
Department of Environmental Technology and Urban Planning, Graduate School of Engineering, Nagoya Institute of Technology, Nagoya 466-8555, Japan. takasu.akinori@nitech.ac.jp
Akinori
A
Takasu
Kazuhiro
K
Iso
Takumi
T
Dohmae
Tadamichi
T
Hirabayashi
D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000737:chemistry; D015374:Biosensing Techniques; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry; D006873:Hydroquinones / Q000138:chemical synthesis / Q000737:chemistry; D037102:Lectins / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011145:Polyvinyls / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility
C510413:1,4-bis(O-2,3,4,6-tetra-O-acetylglucopyranosyl)-2,5-dibromobenzene; C510412:2,5-dibromo-4-methoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxyglucopyranoside; D002241:Carbohydrates; D005960:Glucosides; D006873:Hydroquinones; D037102:Lectins; D011145:Polyvinyls; C510411:poly(2,5-bis(O-glucopyranosyl)-4-phenylenevinylene-alt-4-phenylenevinylene); C510410:poly(2-(O-(2-acetamido-2-deoxyglucopyranosyl))-5-methoxy-4-phenylenevinylene-alt-4-phenylenevinylene); C470024:poly(4-phenylenevinylene); D000117:Acetylglucosamine