A novel soluble aminocellulose derivative type: its transparent film-forming properties and its efficient coupling with enzyme proteins for biosensors

P. Berlin et al., A novel soluble aminocellulose derivative type: its transparent film-forming properties and its efficient coupling with enzyme proteins for biosensors, MACRO CH P, 201(15), 2000, pp. 2070-2082
Citations number
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ISSN journal
1022-1352 → ACNP
Year of publication
2070 - 2082
SICI code
By means of the reaction of 6-tosylcellulose derivatives with diamino compo unds, it has been possible to provide a new soluble and film-forming aminoc ellulose-derivative type with a diamine residue at C-6 of the ase unit (AGU ) and with so-called solubilizing groups, such as acetate, benzoate, carban ilate, methoxy and/or tosylate groups at C-2/C-3. For example, aminocellulo se derivatives were synthesized with aliphatic diamine residues of differen t alkyl chain lengths ((CH2)(m) with m = 2, 4, 6, 8, 12) at C-6. Other new aminocellulose derivatives were those with an aromatic diamine residue, e.g ., 1,4-phenylenediamine or benzidine residue and others,at C-6. Depending o n the structure of the diamine residue at C-6 and of the substituents at C- 2/C-3 the aminocellulose derivatives were solutions in various solvents, mo stly in N,N-dimethylacetamide (DMA) or dimethylsulfoxide (DMSO). Aminocellu loses with a diaminoethane or diaminobutane residue at C-6 and methoxy grou ps at C-2/C-3 were soluble in water All the amino celluloses synthesized fo rmed transparent films from their solutions. These aminocelluloses apparent ly, form superstructures or so-called supramolecular architectures accordin g to a structure-inherent organization principle, which became visible, for example, in the case of PDA cellulose tosylates (in DMA) as gel-like aggre gates after approx. 1 week of storage at 4 degreesC. The superstructures or aggregates could be imaged on the aminocellulose film surface by atomic fo rce microscopy (AFM) in the form of characteristic topographic structures, e.g. as "hole" structures. In this way, structural and environment-induced factors influencing the aggregate formation were The transparent aminocellu lose films were excellently suited for covalent coupling with oxidoreductas e enzymes such as glucose oxidase (GOD), lactate oxidase (LOD), peroxidase (POD) via bifunctional compounds. A number of new bifunctional enzyme coupl ing reactions, e.g. via L-ascorbic acid or benzenedisulfonic dichlorides fo rming amide or sulfonamide coupling structures led to functionally stable n anostructure building blocks with recognition patterns in the case of GOD a nd POD coupling to PDA cellulose tosylate films. The PDA cellulose derivatives proved to be promising cellulose structural u nits because the redox-chromogenic PDA residue at C-6 provides the derivati ves with a wide range of reaction possibilities. e.g. diazo coupling reacti ons, NH2-reactive coupling reactions and oxidative coupling reactions to re dox dyes.