Disease relevance of Amination

• Tetanus toxoid was conjugated to the polysaccharide by reductive amination, via the free aldehyde groups present on the partially oxidized sialic acid residues [1].
• Haemophilus influenzae type b (Hib) capsular polysaccharide (PRP) was selectively hydrolyzed to reducing oligosaccharides, and the fraction containing 3-10 ribosylribitolphosphate repeating units (VS) was conjugated by reductive amination to diphtheria toxin (DTx), its nontoxic derivative CRM197 (Dcr), or diphtheria toxoid (DTd) [2].
• Escherichia coli S-adenosylmethionine decarboxylase. Subunit structure, reductive amination, and NH2-terminal sequences [3].
• Reducing oligosaccharides from the Haemophilus influenzae type b capsular polymer (PRP) coupled by reductive amination to diphtheria toxoids (DTd) had been shown to elicit potentially protective serum anti-PRP antibodies (Ab) in infants too young for an adequate response to PRP vaccine [4].
• Serologically reactive O-polysaccharide from nine serotypes of Pseudomonas aeruginosa were covalently linked to toxin A via reductive amination, with adipic acid dihydrazide serving as a spacer molecule [5].

Psychiatry related information on Amination

• Synthesis of 4,5-dianilinophthalimide and related analogues for potential treatment of Alzheimer's disease via palladium-catalyzed amination [6].

High impact information on Amination

• Isomaltose oligosaccharides varying in size from two sugars, isomaltose (IM2), to seven sugars, isomaltohepatose (IM7), were coupled to stearylamine by reductive amination with sodium cyanoborohydride [7].
• Type III polysaccharide was covalently coupled to beta C protein by reductive amination [8].
• Editing the stereochemical elements in an iridium catalyst for enantioselective allylic amination [9].
• The receptor specificity of the plant seed toxin ricin, which ordinarily binds to galactose-containing receptors, has been altered by coupling monophosphopentamannose residues to ricin by reductive amination and by reversibly binding lactose to the modified ricin [10].
• The optimal procedure involved ozone cleavage of the double bond of GD3 in the ceramide backbone, introducing an aldehyde group, and coupling to aminolysyl groups of proteins by reductive amination [11].

Chemical compound and disease context of Amination

• Oligosaccharides of smooth-type lipopolysaccharide (LPS) and oligosaccharides of rough-type LPS were isolated from Haemophilus pleuropneumoniae and conjugated to tetanus toxoid by reductive amination [12].
• In Escherichia coli K-12, two enzymes, encoded by ilvE and tyrB, catalyze the amination of 2-ketoisocaproate (2-KIC) to form leucine [13].
• Erwinia carotovora L-asparaginase was conjugated via the epsilon-amino groups of its lysine residues with colominic acid (CA) (polysialic acid) of average molecular mass of 10 kDa by reductive amination in the presence of NaCNBH3 [14].
• Neisseria meningitidis serogroup C polysaccharide (CCPS) was conjugated to the carrier protein P64k using two different conjugation procedures, condensation mediated by carbodiimide with adipic acid dihydrazide as spacer and the reductive amination method [15].
• Extracts of Streptomyces fradiae 75-078, a producer of an antibiotic neomycin, were found to catalyze three reactions which are included in the proposed biosynthetic pathway to 2-deoxystreptamine; amination of deoxyinosose yielding deoxyinosamine, conversion of deoxyinosamine to 2-deoxystreptamine and deamination of 2-deoxystreptamine [16].

Biological context of Amination

• The enzyme catalyzes the oxidative deamination of L-leucine, L-valine, L-isoleucine, L-norvaline, L-alpha-aminobutyrate, and L-norleucine, and the reductive amination of their keto analogues [17].
• These data suggest that Cys104 is an essential residue involved in the hydrolysis of glutamine to produce an amino group and is not needed for the hydrolysis of ATP or amination of xanthosine 5'-monophosphate to produce GMP [18].
• Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac(2)O, NEt(3), 130 degrees C) [19].
• The free radical-mediated aryl amination was sequenced with the O'Donnell phase transfer-catalyzed enantioselective alkylation strategy of glycinyl imine to provide either enantiomer of indoline alpha-amino acids with high ee [20].
• A range of substituted fumaric and aspartic acid substrates for the enzyme 3-methylaspartate ammonia-lyase (EC 4.3.1.2) have been synthesized and used to study the kinetics of the catalyzed reaction in both the forward (deamination) and reverse (conjugative amination) reaction directions [21].

Anatomical context of Amination

• Treatment of synaptosomes with veratridine stimulated reductive amination of 2-oxoglutarate during the early time points [22].
• When the NADH content of hepatocytes was increased by 3-hydroxybutyrate, the addition of NH4Cl and/or alpha-methylisocitrate caused a decline in NADH (and NADPH) content, suggesting that reducing equivalents from NADH as well as from NADPH can support net reductive amination of 2-oxoglutarate when required for urea synthesis [23].
• These observations suggest that ammonia trapping in skeletal muscle is coupled to glutamine formation via amination of glutamic acid [24].
• The second approach consisted of using heparin, a mucopolysaccharide with a strong affinity towards ATIII, coupled to amine-modified or epoxy-activated membranes by reductive amination, for the purification of rATIII [25].
• Pneumococcal type 19F polysaccharide was conjugated to various proteins, i.e., bovine serum albumin, human immunoglobulin, and pneumococcal R61 cell wall protein, by the method of reductive amination [26].

Associations of Amination with chemical compounds

• Ten aryl carbohydrate adducts were synthesized by the reductive amination of a carbohydrate with an aryl amine, using sodium cyanoborohydride as a reducing agent [27].
• Experiments do not support a recent claim that glutamate formed from the amination of citric acid cycle-derived alpha-ketoglutarate is a messenger in glucose-induced insulin secretion (Maechler, P., and Wollheim, C. (1999) Nature 402, 685-689) [28].
• On the mechanism of glutamine-dependent reductive amination of alpha-ketoglutarate catalyzed by glutamate synthase [29].
• In the reverse reaction, hydroxypyruvate is aminated to serine but very inefficiently relative to the amination of pyruvate to alanine [30].
• The aminopropanol moiety is derived in a hitherto unknown pathway from pyruvate by reductive amination [31].

Gene context of Amination

• These mutants required cytidine for growth, proving that in L. lactis, the pyrG product is the only enzyme responsible for the amination of UTP to CTP [32].
• Glutamate synthesized by GDH via reductive amination is the amino group donor for alanine synthesis and the precursor required for proline synthesis [33].
• GMP synthetase (EC 6.3.5.2) is an amidotransferase that catalyzes the amination of xanthosine 5'-monophosphate to form GMP in the presence of glutamine and ATP [18].
• GSI is responsible for the ATP-dependent amination of glutamate to produce glutamine, which is required in the formation of amino acids, purines and pyrimidines [34].
• METHODS: EGF was coupled to periodate activated dextran by reductive amination [35].

Analytical, diagnostic and therapeutic context of Amination

• Oligosaccharides were derivatized by reductive amination with benzylamine followed by N,N-dimethylation with methyl iodide and analyzed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS) and MALDI post-source decay (PSD) TOFMS [36].
• After high-pH anion-exchange chromatography with ion suppression, collected oligosaccharides were analyzed by fast-atom bombardment mass spectrometry after conversion to permethyl derivatives or after reductive amination with rho-aminobenzoic acid ethyl ester [37].
• High affinity heparin oligosaccharides (HA-heparin, anti-factor Xa activity of 592 +/- 120 IU/mg) prepared by partial deaminative cleavage of commercial crude heparin and fractionated by agarose-ATIII affinity chromatography, were immobilized to surface-modified PE by reductive amination [38].
• Selective purification of reduced oligosaccharides using a phenylboronic acid bond elut column: potential application in HPLC, mass spectrometry, reductive amination procedures and antigenic/serum analysis [39].
• The depolymerization of heparin resulted in a loss of biological activity which outweighed the increase in the terminal amine groups (produced by reductive amination), that were used for glutaraldehyde immobilization to the PVA [40].

References