PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
3322103-2	1987	To preclude any carbohydrate-dependent binding to the sugar residues on the glycoprotein peroxidase, the enzyme has to be treated with sodium periodate and sodium cyanoborohydride prior to coupling, which results in oxidative cleavage of the carbohydrates and reduction of the aldehydes thus formed to primary alcohols.	sodium cyanoborohydride	156-179	LOW QUALITY PROTEIN: peroxidase 60	Ricinus communis	89-99
3126263-7	1988	The covalent linkage to membranes of unlabelled Ro 16-6491 and Ro 19-6327 (a selective and reversible MAO-B inhibitor closely related to Ro 16-6491) after the addition of NaBH3CN at pH 4.5 irreversibly inactivated MAO-B activity whereas MAO-A activity was unaffected.	sodium cyanoborohydride	171-178	monoamine oxidase B	Homo sapiens	102-107
3126814-1	1988	Reductive methylation of bovine brain derived acidic fibroblast growth factor (aFGF) with formaldehyde and sodium cyanoborohydride reduces its capacity to stimulate mitogenesis in Balb/C 3T3 cells, and this correlates with the modification of less than 3 of its 12 lysine residues.	sodium cyanoborohydride	107-130	fibroblast growth factor 1	Mus musculus	46-77
3126814-1	1988	Reductive methylation of bovine brain derived acidic fibroblast growth factor (aFGF) with formaldehyde and sodium cyanoborohydride reduces its capacity to stimulate mitogenesis in Balb/C 3T3 cells, and this correlates with the modification of less than 3 of its 12 lysine residues.	sodium cyanoborohydride	107-130	fibroblast growth factor 1	Bos taurus	79-83
6404224-2	1983	Heterozygous and homozygous glycophorin A were partially and fully reductively methylated with 13C-enriched formaldehyde in the presence of sodium cyanoborohydride.	sodium cyanoborohydride	140-163	glycophorin A (MNS blood group)	Homo sapiens	28-41
6207049-3	1984	Reacting sodium cyanoborohydride with gossypol reduces its affinity for AFP, showing that intact aldehyde groups on gossypol are important for binding to rat AFP and indicating that gossypol is specifically inter-acting with a nucleophilic site on AFP that influences estrogen binding.	sodium cyanoborohydride	9-32	alpha-fetoprotein	Rattus norvegicus	72-75
6207049-3	1984	Reacting sodium cyanoborohydride with gossypol reduces its affinity for AFP, showing that intact aldehyde groups on gossypol are important for binding to rat AFP and indicating that gossypol is specifically inter-acting with a nucleophilic site on AFP that influences estrogen binding.	sodium cyanoborohydride	9-32	alpha-fetoprotein	Rattus norvegicus	158-161
6207049-3	1984	Reacting sodium cyanoborohydride with gossypol reduces its affinity for AFP, showing that intact aldehyde groups on gossypol are important for binding to rat AFP and indicating that gossypol is specifically inter-acting with a nucleophilic site on AFP that influences estrogen binding.	sodium cyanoborohydride	9-32	alpha-fetoprotein	Rattus norvegicus	158-161
6317019-1	1983	Pulmonary angiotensin converting enzyme has been reductively methylated by using formaldehyde and sodium cyanoborohydride.	sodium cyanoborohydride	98-121	angiotensin I converting enzyme	Homo sapiens	10-39
6411646-2	1983	Reductive methylation of the three amino groups of porcine insulin was accomplished by incubation with formaldehyde and sodium cyanoborohydride.	sodium cyanoborohydride	120-143	insulin	Homo sapiens	59-66
32784502-4	2020	Facile acetal epimerization at the C-6 position in 1,2-oxazine ring was observed in the course of reduction with NaBH3CN in AcOH.	sodium cyanoborohydride	113-120	complement C6	Homo sapiens	35-38
6284736-3	1982	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.	sodium cyanoborohydride	75-98	complement C2	Homo sapiens	13-16
6315502-1	1983	The sialic acid residues of human alpha 1-protease inhibitor were modified by periodate oxidation and subsequent reductive amination with ethanolamine and sodium cyanoborohydride.	sodium cyanoborohydride	155-178	serpin family A member 1	Homo sapiens	34-60
7364757-2	1980	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.	sodium cyanoborohydride	279-302	SEC14 like lipid binding 2	Homo sapiens	0-26
7364757-2	1980	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.	sodium cyanoborohydride	279-302	SEC14 like lipid binding 2	Homo sapiens	28-31
571815-0	1979	Reductive methylation of IF-3 and EFTu with [14C]formaldehyde and sodium cyanoborohydride.	sodium cyanoborohydride	66-89	Tu translation elongation factor, mitochondrial	Homo sapiens	34-38
21538-1	1977	Reductive alkylation of bovine serum albumin (BSA) and wool by a aromatic aldehydes and sodium cyanoborohydride has been investigated.	sodium cyanoborohydride	88-111	albumin	Homo sapiens	31-44
28872849-4	2017	Meanwhile, [Au18(Dppm)6Br4](BPh4)2 could be converted into [Au13(Dppm)6](BPh4)3 and [Au20(Dppm)6(CN)6] by engineering the surface ligands under excess PPh3 or moderate NaBH3CN, respectively.	sodium cyanoborohydride	168-175	caveolin 1	Homo sapiens	151-155
31765132-1	2019	In recent years, salts of the hydridotricyanoborate anion [BH(CN)3]- (MHB) have become readily available.	sodium cyanoborohydride	59-66	MHB	Homo sapiens	70-73
23339688-22	2013	These results account for the uridine nucleotide-dependence in the reduction of [GalE-NAD] by glucose or NaBH3CN.	sodium cyanoborohydride	105-112	UDP-galactose-4-epimerase	Homo sapiens	81-85
27903233-2	2017	In the current study beta-casein was glycated in the presence of D-glucose and sodium cyanoborohydride as a reducing agent.	sodium cyanoborohydride	79-102	casein beta	Bos taurus	21-32
26842584-5	2016	METHODS: Released N-glycans from the glycoproteins bovine fetuin, ribonuclease B, chicken ovalbumin, and porcine thyroglobulin were reduced with sodium cyanoborohydride and both negative ion CID spectra and ion mobility properties of their phosphate adducts were examined with a Waters Synapt G2Si travelling-wave ion mobility mass spectrometer with electrospray sample introduction.	sodium cyanoborohydride	145-168	ovalbumin (SERPINB14)	Gallus gallus	90-99
26954725-2	2016	The reaction was effectively catalyzed by the ligand-free Cu(OTf)2 and afforded the intended amine derivatives in good yields after treatment of NaBH3CN.	sodium cyanoborohydride	145-152	POU class 2 homeobox 2	Homo sapiens	58-66
16872167-4	2006	Finally, a highly stereoselective entry to 2-(aminomethyl)-2-chloroaziridines 27 (70-98% yield; de > 95-99) was worked out from the reaction of cis-3-aryl-2-chloro-2-imidoylaziridines 19 and sodium cyanoborohydride in the presence of acetic acid.	sodium cyanoborohydride	194-217	suppressor of cytokine signaling 3	Homo sapiens	147-152
18550580-4	2008	Direct covalent complex formation between the CrA-PdG adduct and Top1 is detectable after reduction with sodium cyanoborohydride, which is consistent with the formation of a Schiff base between Top1 and the ring open aldehyde form of the adduct.	sodium cyanoborohydride	105-128	myotubularin related protein 11	Homo sapiens	46-49
21375808-3	2012	To specifically target genes to asialoglycoprotein receptor of hepatocytes, a galactose moiety was combined into the poly(ethylene glycol) (PEG)-terminal end by reductive coupling using lactose and sodium cyanoborohydride.	sodium cyanoborohydride	198-221	progestagen associated endometrial protein	Homo sapiens	140-143
12948125-7	2003	In comparison with THB, amineboranes and NaBH3CN allowed, in general, a better control of interference effects of Fe(III), Ni(II), Co(II), and Cu(II).	sodium cyanoborohydride	41-48	mitochondrially encoded cytochrome c oxidase II	Homo sapiens	131-136
15264873-4	2004	LSA was synthesized by conjugating lactose to human serum albumin by the formation of a Schiff"s base and successive reduction with sodium cyanoborohydride.	sodium cyanoborohydride	132-155	albumin	Rattus norvegicus	52-65
8652633-2	1996	The oxidized CA was then coupled to catalase by reductive amination in the presence of sodium cyanoborohydride.	sodium cyanoborohydride	87-110	catalase	Homo sapiens	36-44
11591524-3	2001	Also described is a new mixed borohydride system, NaBH4-LiOTf-NMP, which works as an alternative to NaBH3CN for the SN2 type displacement.	sodium cyanoborohydride	100-107	solute carrier family 38 member 5	Homo sapiens	116-119
10652987-2	1999	HDL-3 were glycated with various glucose concentrations (0-200 mM) for 3 d at 37 degrees C with sodium cyanoborohydride as reducing agent and antioxidants.	sodium cyanoborohydride	96-119	HDL3	Homo sapiens	0-5
9894014-6	1999	When phospholipid model systems and cell membranes were exposed to physiological levels of L-tyrosine and the myeloperoxidase/hydrogen peroxide/chloride system followed by treatment with NaBH3CN, reduced Schiff base adducts of pHA with ethanolamine glycerophospholipid and serine glycerophospholipid (pHA-PE and pHA-PS, respectively) were produced.	sodium cyanoborohydride	187-194	myeloperoxidase	Homo sapiens	110-125
11599936-15	2001	HPLC analysis of reaction mixtures treated with NaBH3CN provided improved conditions for adduct identification, which should be useful for in vivo studies of DNA adduct formation by NPYR.	sodium cyanoborohydride	48-55	C-X-C motif chemokine receptor 4	Homo sapiens	182-186
10571272-2	1999	METHODS: Bovine insulin was allowed to react with cis-9-hexadecenal in an aqueous-organic medium in the presence of NaBH3CN at room temperature overnight.	sodium cyanoborohydride	116-123	insulin	Bos taurus	16-23
9895041-6	1999	Immunization of rabbits with products of the reaction of bovine serum albumin with acetaldehyde led to the generation of antibodies that reacted to reduced adducts formed in the reaction of acetaldehyde and proteins in the presence of sodium cyanoborohydride.	sodium cyanoborohydride	235-258	albumin	Oryctolagus cuniculus	64-77
8823904-1	1996	The reducing end C-1 of (1-->4)-linked alpha-D-oligogalacturonides (oligogalacturonides), with degrees of polymerization (dp) 3 and 13, was coupled to tyramine via reductive amination in the presence of sodium cyanoborohydride.	sodium cyanoborohydride	206-229	heterogeneous nuclear ribonucleoprotein C	Homo sapiens	17-20
8665924-2	1996	The pseudosubstrate inhibitor N-[2-aminoethyl]-5-chloro-2-pyridine carboxamide HCl (lazabemide) can be irreversibly linked to MAO-B by reduction of the enzyme-inhibitor complex with NaBH(3)CN.	sodium cyanoborohydride	182-191	monoamine oxidase B	Homo sapiens	126-131
8483897-5	1993	Human serum albumin and excess tolmetin glucuronide were coincubated in the presence of sodium cyanoborohydride to trap imine intermediates.	sodium cyanoborohydride	88-111	albumin	Homo sapiens	12-19
2314388-15	1990	The present results indicate that [3H]Ro 41-1049 is incorporated into a subunit of MAO-A, in the presence of NaBH3CN, and modifies a protein domain that is essential for the enzyme activity.	sodium cyanoborohydride	109-116	monoamine oxidase A	Homo sapiens	83-88
2170216-3	1990	HDL3 was glycosylated in vitro with glucose alone or in combination with sodium cyanoborohydride.	sodium cyanoborohydride	73-96	HDL3	Homo sapiens	0-4
2574996-4	1989	In order to investigate the mechanism by which the cytolysin causes cell lysis, we have prepared a highly active [3H]cytolysin derivative by reductive methylation with sodium cyanoborohydride and [3H]formaldehyde.	sodium cyanoborohydride	168-191	perforin 1	Homo sapiens	51-60
2574996-4	1989	In order to investigate the mechanism by which the cytolysin causes cell lysis, we have prepared a highly active [3H]cytolysin derivative by reductive methylation with sodium cyanoborohydride and [3H]formaldehyde.	sodium cyanoborohydride	168-191	perforin 1	Homo sapiens	117-126
2605311-4	1989	Reduction with sodium cyanoborohydride is much gentler and gives solutions with less than 5% methemoglobin.	sodium cyanoborohydride	15-38	hemoglobin subunit gamma 2	Homo sapiens	93-106