Unreferenced stub auto yes date December 2009 Image Cyclic hemiaminal ether.svg thumb 120px Cyclic hemiaminal ether bond derived from an aldehyde Glycosylamine is a biochemical compound consisting of an amine with a Glycosidic bond N glycosidic bond to a carbohydrate , thus forming a cyclic hemiaminal ether bond aminoether . Examples include nucleosides such as adenosine . Image Adenosin.svg thumb 150px left The nucleoside adenosine Examples Ribofuranosylamine Category Biomolecules Category Carbohydrates Biochem stub fr Glycosylamine ... more details
The Amadori rearrangement is an organic reaction describing the acid catalysis acid or base catalyzed isomerization or rearrangement reaction of the N glycoside of an aldose or the glycosylamine to the corresponding 1 amino 1 deoxy ketose . ref W. Amadori, Atti. reale accad. nazl. Lincei, 6 2, 337 1925 6 9, 68, 226 1929 6 13, 72 1931 ref ref Strategic Applications of Named Reactions in Organic Synthesis Paperback by Laszlo Kurti, Barbara Czako ISBN 0 12 429785 4 ref The reaction is important in carbohydrate chemistry . The reaction mechanism is demonstrated starting from the reaction of D mannose in its closed 1 and open form 2 with ammonia the 1,1 amino alcohol 3 , which is unstable and loses water to the glycosylamine again the open imine 5 and the closed form hemiaminal 4 , which is the starting point for the actual Amadori rearrangement. ref Mutarotation, Hydrolysis, and Rearrangement Reactions of Glycosylamines HORACE S. ISBELL and HARRIET L. FRUSH J. Org. Chem. 1958 , 23 9 , 1309 1319. DOI 10.1021 jo01103a019 ref File AmadoriRearrangement1.png 500px center The Amadori Rearrangement By treatment of the glycosylamine with pyridine and acetic anhydride , the imine group rearranges and the intermediate enol , in turn, rearranges to the ketone . In this particular reaction, the all alcohol and amino groups are acylation acylated as well. The reaction is associated with the Maillard reaction with reagents naturally occurring sugars and amino acid s. Amadori product An Amadori product is an intermediate in the production of an Advanced glycation endproduct advanced glycation end product AGE as a result of glycation . The formation of an advanced glycation end product involves the following steps Formation of a Schiff base For example the aldehyde group of a glucose molecule will combine with the amino group of a lysine molecule in a protein to form an imine or Schiff base, which is a Covalent bond double bond between the carbon atom of the glucose and the nitrogen at ... more details
Unreferenced date December 2009 Image Aminal 2D skeletal.png thumb right 120px Generic aminal An aminal or aminoacetal is a functional group or type of chemical compound that has two amine groups attached to the same carbon atom C NR sub 2 sub NR sub 2 sub . Again R can be hydrogen or an alkyl group. The aminal and the hemiaminal groups are the cousins of hemiacetal s and acetal s with nitrogen replaced by oxygen . Aminals are encountered in for instance the Fischer indole synthesis . Hemiaminal ethers Image Hemiaminal ether aldehyde.svg thumb 120px Hemiaminal ether derived from an aldehyde File Hemiaminal ether ketone.svg thumb 120px Hemiaminal ether derived from a ketone Hemiaminal ether s are also sometimes called aminals although it is discouraged by the IUPAC. They have the following structure R C NR sub 2 sub OR R . The glycosylamine s are examples of cyclic hemiaminal ethers. See also Hemiaminal Category Functional groups es Aminal fr Aminal nl Aminal scheikunde ja ... more details
Unreferenced date December 2009 Here is a table of data skip past it to edit the text. border 1 cellpadding 2 cellspacing 0 align right style margin left 1em align center valign bottom Nitrogenous base Nucleoside Deoxynucleoside align center valign Image Adenine chemical structure.png 58px Chemical structure of adenine br Adenine br Image Adenosine.png 95px Chemical structure of adenosine br Adenosine br A Image dA chemical structure.png 95px Chemical structure of deoxyadenosine br Deoxyadenosine br dA align center valign Image Guanine chemical structure.png 86px Chemical structure of guanine br Guanine br Image G chemical structure.png 123px Chemical structure of guanosine br Guanosine br G Image dG chemical structure.png 123px Chemical structure of deoxyguanosine br Deoxyguanosine br dG align center valign Image Thymine chemical structure.png 63px Chemical structure of thymine br Thymine br Image T chemical structure.png 87px Chemical structure of 5 methyluridine br 5 Methyluridine br m sup 5 sup U Image dT chemical structure.png 87px Chemical structure of thymidine br Thymidine br dT align center valign Image Uracil chemical structure.png 51px Chemical structure of uracil br Uracil br Image U chemical structure.png 87px Chemical structure of uridine br Uridine br U Image dU chemical structure.png 87px Chemical structure of deoxyuridine br Deoxyuridine br dU align center valign Image Cytosine chemical structure.png 51px Chemical structure of cytosine br Cytosine br Image C chemical structure.png 87px Chemical structure of cytidine br Cytidine br C Image dC chemical structure.png 87px Chemical structure of deoxycytidine br Deoxycytidine br dC Nucleosides are glycosylamine s consisting of a nucleobase often referred to as simply base bound to a ribose or deoxyribose sugar via a anomer beta Glycosidic bond glycosidic linkage . Examples of nucleosides include cytidine , uridine , adenosine , guanosine , thymidine and inosine . Nucleosides can be phosphorylation phosph ... more details
Encyclopedia
top
