Disease relevance of EINECS 247-317-2

• Hepatitis B surface antigens (HBsAg) of both the adw and ayw subtypes were reductively methylated with formaldehyde in the presence of sodium cyanoborohydride [1].
• Incubation of Escherichia coli 5-enolpyruvylshikimate 3-phosphate synthase with its substrate analogue pyruvate in the presence of sodium cyanoborohydride resulted in a significant decrease in its enzyme activity [2].
• Hydrophobic conjugates of a series of aldoses have been prepared by reductive amination with octadecylamine and sodium cyanoborohydride, as model compounds for the analysis of reductively aminated oligosaccharides derived from capsular polysaccharides of Streptococcus pneumoniae [3].
• Clostridium pasteurianum 2(4Fe-4S) ferredoxin has been reductively methylated using [13C]formaldehyde and sodium cyanoborohydride [4].

High impact information on EINECS 247-317-2

• Glycosylation with sodium cyanoborohydride at high pH in borate buffer is a simple, reproducible procedure [5].
• Ten aryl carbohydrate adducts were synthesized by the reductive amination of a carbohydrate with an aryl amine, using sodium cyanoborohydride as a reducing agent [6].
• 1) A radiolabeled DNA substrate is used to tag the active site of Fpg protein, using sodium cyanoborohydride [7].
• Upon reaction of endonuclease V with [14C]formaldehyde (14CH2O) in the presence of the reducing agent sodium cyanoborohydride (Na-CNBH3), it was discovered that 0.8 methylation/endonuclease V molecule was required to reduce both the glycosylase and the phosphodiester lyase activities by 70-80% [8].
• HDL3 was glycosylated in vitro with glucose alone or in combination with sodium cyanoborohydride [9].

Biological context of EINECS 247-317-2

• Labeling of proteins by reductive methylation using sodium cyanoborohydride [10].
• Supernatant Protein Factor (SPF), a protein that enhances the activities of microsomal squalene epoxidase and 2,3-oxidosqualene-lanosterol cyclase, has been labeled either by acylation with N-succinimidyl[2,3-3H]propionate or by reductive methylation with [14C]-formaldehyde and sodium cyanoborohydride [11].
• Analogues were obtained in normal yields via a combination of sodium cyanoborohydride mediated reductive alkylation of resin-bound peptide amine with a tert-butoxycarbonyl amino acid aldehyde for introduction of a CH2NH bond and normal solid-phase peptide chemistry [12].
• Amino sugars released from strong acid hydrolysis of oligosaccharides and glycoproteins were reacetylated and derivatized with 8-aminopyrene-1,3,6-trisulfonate (APTS) along with neutral sugars in the presence of sodium cyanoborohydride to yield quantitatively the highly stable fluorescent APTS adducts [13].

Anatomical context of EINECS 247-317-2

• It should also be possible to demonstrate Schiff base formation occurring between accessory cells and lymphocytes directly and definitively by means of specific reduction with sodium cyanoborohydride [14].
• Halorhodopsin was reconstituted in these membranes with tritium-labeled retinal and the preparation was reduced with sodium cyanoborohydride [15].
• 5) The weak reducing agent sodium cyanoborohydride which is specific for Schiff bases at neutral pH inhibited both Ag-induced and periodate-induced T cell activation [14].
• When treated with this affinity label in the presence of sodium cyanoborohydride to reduce Schiff bases, neutrophil cytosol was shown to lose at least 90% of its activity in the cell-free system [16].
• The chemistry of the collagen cross-links. Characterization of the products of reduction of skin, tendon and bone with sodium cyanoborohydride [17].

Associations of EINECS 247-317-2 with other chemical compounds

• Apoenzyme must be treated, under mildly acidic conditions (pH = 6), at a relatively low molar ratio of formaldehyde to protein (40:1); and, upon reduction with sodium cyanoborohydride, 85% of the formaldehyde is incorporated at Lysine 258 and 15% at the amino-terminal alanyl residue [18].
• The affinity columns were prepared in two steps: (a) direct reductive amination of the disaccharide and aminoethyl gel with sodium cyanoborohydride in aqueous solution at pH 9; (b) N-acetylation of excess amino groups [19].
• The selective carboxymethylation of the N-terminal amino groups of hemoglobin A with glyoxylic acid and sodium cyanoborohydride has been studied as a function of the state of ligation of hemoglobin [20].
• The method consisted of incubating cell extracts with 3H-decarboxylated S-adenosylmethionine and sodium cyanoborohydride in the presence of a spermidine synthase inhibitor [21].
• Carbohydrate modifications were performed in PBS (pH 6.2) by first oxidizing the antibody with sodium periodate followed by incubation with hydrazide-terminated PEG followed by reduction with sodium cyanoborohydride [22].

Gene context of EINECS 247-317-2

• The fragment C-2 has now been selectively methylated with formaldehyde and sodium cyanoborohydride to give the epsilon-dimethylamino derivatives of Lys-30, 40, and 41 in 96-99% average yield [23].
• Reductive methylation of IF-3 and EFTu with [14C]formaldehyde and sodium cyanoborohydride [24].
• Inactivation of 5-enolpyruvylshikimate 3-phosphate synthase by its substrate analogue pyruvate in the presence of sodium cyanoborohydride [2].
• On the other hand, reductive methylation of lysozyme by formaldehyde and sodium cyanoborohydride was considered suitable for radiolabeling of lysozyme [25].
• Sodium borohydride and sodium cyanoborohydride were assessed as potential reagents for determining ligand-induced changes in accessibility to the active-site of aspartate aminotransferase [26].

Analytical, diagnostic and therapeutic context of EINECS 247-317-2

• Incubation of [2,8-3H]ATPDA with the enzyme followed by reduction with sodium cyanoborohydride, proteolysis with trypsin, and separation of the resulting peptides by high pressure liquid chromatography yielded two labeled peptide fractions [27].
• An additional improvement in sensitivity (up to 10-fold) results from an increase in the binding of 125I-wheat germ agglutinin to sialic acid-containing glycoproteins after treatment of the blots with 5 mM sodium metaperiodate followed by 5 mM aniline in the presence of 30 mM sodium cyanoborohydride [28].
• The efficiencies in derivatization of reducing carbohydrates were compared by capillary electrophoresis using maltose as a model with nine monoaminobenzene derivatives by reductive amination in the presence of sodium cyanoborohydride [29].
• Formaldehyde adducts, stabilized by sodium cyanoborohydride reduction to methylamines, were separated by Sepharose 2B gel filtration [30].
• Following reduction of Schiff bases with sodium cyanoborohydride, biotinylated proteins were selected from cell lysates with avidin affinity chromatography [31].

References