Glucose with amino groups

In this work, we have grafted the mesoporous SBA-15 materials with 3-aminopropyl trimethoxysilane [10], In a subsequent step, the aminopropyl moiety was reacted with glutardialdehyde, which reacts also with amino groups of the enzymes chloroperoxidase (CPO) and glucose oxidase (GOx) (Scheme 1). 

Hisamtsu, I., Kataoka, K., Okano, T. and Sakurai, Y. (1997) Glucose-responsive gel from phenylborate polymer and poly (vinyl alcohol) Prompt response at physiological pH through the interaction of borate with amino group in the gel. Pharm. Res., 14 289-293. 

Derived from oxidative modification of triose phosphate during glucose metabolism model for glycation of proteins reacts with amino groups in proteins and nucleic acids involved in advanced glycation endproducts. 

Diabetics are at special risk for cardiovascular disease apparently because diabetes results in chronically elevated levels of plasma glucose. Glucose exists in ring and openopen-chain form has an aldehyde group that readily can condense with amino groups such as those of proteins. The condensation product formed by an aldehyde and an amino group is called a Schiff base,... 

As is tile case for other aldehydes, acetaldehyde can condense with amino groups to form a Schiff base. Schiff base formation occurs in a number of pathological conditions. For example, breakdown of polyunsaturated fatty adds may generate malondialdehyde, which reacts with proteins to produce damage. To review another example, the elevated plasma glucose levels in diabetes results in an increased condensation of glucose, via a Schiff base, with various proteins in the bloodstream. Aldehyde damage to proteins has been reviewed by Stadtman (1990). 

Glucose is reactive because of the presence of an aldehyde group in its open-chain form. The aldehyde group slowly condenses with amino groups to form Schiff-base adducts. 

The amino alcohols 429 and 430 (prepared from diacetone-D-glucose, the amino group introduced by displacing a C-6 tosyl, and 430 prepared by deoxygenation of C-3) catalysed (at 5 mol%) diethylzinc addition to several aldehydes but with e.e.s of only 9-46% S products predominated). ... 

The dominant interactions that take place with this novel phase are not clear. There will obviously be dispersive interactions with the propyl chain and some polar interactions with the amino group. Whether there are ionic interactions taking place as well is uncertain but, nevertheless, the material affects an excellent separation of glucose and fructose and this remains a baseline separation even when the two sugars are both present at about the 5% level. 

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