1946-82-3Relevant articles and documents
Preprogramming Complex Hydrogel Responses using Enzymatic Reaction Networks
Postma, Sjoerd G. J.,Vialshin, Ilia N.,Gerritsen, Casper Y.,Bao, Min,Huck, Wilhelm T. S.
supporting information, p. 1794 - 1798 (2017/02/05)
The creation of adaptive matter is heavily inspired by biological systems. However, it remains challenging to design complex material responses that are governed by reaction networks, which lie at the heart of cellular complexity. The main reason for this slow progress is the lack of a general strategy to integrate reaction networks with materials. Herein we use a systematic approach to preprogram the response of a hydrogel to a trigger, in this case the enzyme trypsin, which activates a reaction network embedded within the hydrogel. A full characterization of all the kinetic rate constants in the system enabled the construction of a computational model, which predicted different hydrogel responses depending on the input concentration of the trigger. The results of the simulation are in good agreement with experimental findings. Our methodology can be used to design new, adaptive materials of which the properties are governed by reaction networks of arbitrary complexity.
Characteristics of early Maillard reaction products by electrospray ionization mass spectrometry
Li, Chuanjiang,Wang, Hui,Zhang, Yinfeng,Juárez, Manuel,Shao, Guangjie,Ruan, Eric Dongliang
, p. 7452 - 7456 (2015/04/22)
It is crucial to characterize early Maillard reaction products and the important compounds formed in the early stage of Maillard reactionas Amadori rearrangement products are the most important modifications in food science. We report here that using electrospray ionization-mass spectrometry (ESI-MS) to directly characterize fragmentation behaviour of Amadori rearrangement products in a reaction model system using six selected amino acids (arginine, asparagine, glutamine, histidine, lysine and tryptophan) and their N-terminal acetylated forms with two reducing disaccharides, lactose and maltose. The fragmentation behaviour of Amadori rearrangement products was illustrated by Tandem MS (MS2) with collision-induced dissociation (CID). Results showed that the sugar moiety was preferentially fragmented, where by the neutral loss of small molecules, such as 18 Da, 36 Da, 216 Da, 246 Da and 324 Da from disaccharide moieties. Among the fragmented ions, [M-246 + H]+ of disaccharides were relatively stable and they were further studied for fragmentation mechanisms based on representatives of lysine and Nα-Ac-lysine. The study is useful to understand the fundamentals of glycation in complex protein systems based on ESI-MS related techniques.
The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates
Munanairi, Admire,O'Banion, Steven K.,Gamble, Ryan,Breuer, Elizabeth,Harris, Andrew W.,Sandwick, Roger K.
, p. 2575 - 2592 (2008/03/27)
Ribose 5-phosphate (R5P) undergoes the Maillard reaction with amines at significantly higher rates than most other sugars and sugar phosphates. The presence of an intramolecular phosphate group, which catalyzes the early stages of the Maillard reaction, provides the opportunity for the R5P molecule to undergo novel reaction paths creating unique Maillard products. The initial set of reactions leading to an Amadori product (phosphorylated) and to an α-dicarbonyl phosphate compound follows a typical Maillard reaction sequence, but an observed phosphate hydrolysis accompanying the reaction adds to the complexity of the products formed. The reaction rate for the loss of R5P is partially dependent on the pKa of the amine but also is correlated to the protonation of an early intermediate of the reaction sequence. In the presence of oxygen, a carboxymethyl group conjugated to the amine is a major product of the reaction of R5P with N-acetyllysine while little of this product is generated in the absence of oxygen. Despite lacking a critical hydroxyl group necessary for the Maillard reaction, 2-deoxyribose 5-phosphate (dR5P) still generates an Amadori-like product (with a carbonyl on the C-3 carbon) and undergoes phosphate cleavage. Two highly UV-absorbing products of dR5P were amine derivatives of 5-methylene-2-pyrrolone and 2-formylpyrrole. The reaction of dR5P with certain amines generates a set of products that exhibit an interesting absorbance at 340 nm and a high fluorescence.
