PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
29555591-3	2018	To further emphasize the significance of this moiety for developing Cu(II) ionophores, we herein designed a beta-diketo analog of piperlongumine, PL-I, characterized by the presence of high proportion of the keto-enol form in dimethylsulfoxide and chloroform, and identified its keto-enol structure by NMR and theoretical calculations.	keto-enol	208-217	amyloid beta precursor protein	Homo sapiens	106-112
29555591-3	2018	To further emphasize the significance of this moiety for developing Cu(II) ionophores, we herein designed a beta-diketo analog of piperlongumine, PL-I, characterized by the presence of high proportion of the keto-enol form in dimethylsulfoxide and chloroform, and identified its keto-enol structure by NMR and theoretical calculations.	keto-enol	208-217	serpin family F member 2	Homo sapiens	146-150
29555591-3	2018	To further emphasize the significance of this moiety for developing Cu(II) ionophores, we herein designed a beta-diketo analog of piperlongumine, PL-I, characterized by the presence of high proportion of the keto-enol form in dimethylsulfoxide and chloroform, and identified its keto-enol structure by NMR and theoretical calculations.	keto-enol	279-288	amyloid beta precursor protein	Homo sapiens	106-112
29555591-3	2018	To further emphasize the significance of this moiety for developing Cu(II) ionophores, we herein designed a beta-diketo analog of piperlongumine, PL-I, characterized by the presence of high proportion of the keto-enol form in dimethylsulfoxide and chloroform, and identified its keto-enol structure by NMR and theoretical calculations.	keto-enol	279-288	serpin family F member 2	Homo sapiens	146-150
20181392-3	2010	Curcumin derivatives with keto-enol tautomerism showed high levels of binding to Abeta aggregates but not to Abeta monomers.	keto-enol	26-35	amyloid beta precursor protein	Homo sapiens	81-86
26376730-3	2015	A beta-phosphorylated nitroxide substrate prototype exhibiting keto-enol equilibrium upon enzymatic activity has been prepared.	keto-enol	63-72	amyloid beta precursor protein	Homo sapiens	0-6
22525098-4	2012	Because previous studies of the related enzyme from bovine liver had suggested loss of the C-5 hydrogen from UDP-gluco-hexodialdose due to keto-enol tautomerism, we examined incorporation of solvent deuterium into product(s) of UDP-glucose oxidation by hUGDH.	keto-enol	139-148	complement C5	Bos taurus	91-94
22434387-4	2012	Our study presents a new approach to extend PHIP to substrates that primarily cannot be hyperpolarized due to a steady intramolecular re-arrangement, the so-called keto-enol tautomerism.	keto-enol	164-173	pleckstrin homology domain interacting protein	Homo sapiens	44-48
29191105-5	2018	Results from the quantitative structure active correlative analysis indicated that methoxy groups and beta-diketone structure possessing keto-enol tautomerism in curcumin were necessary to inhibit AhR transformation, and the addition of methyl and methoxy group(s) to the curcumin increased the inhibition effect.	keto-enol	137-146	aryl hydrocarbon receptor	Homo sapiens	197-200
27897077-1	2017	Acetylcholinesterase (AChE) is an important enzyme responsible for Alzheimer"s disease, as per report, keto-enol form of curcumin inhibits this enzyme.	keto-enol	103-112	acetylcholinesterase (Cartwright blood group)	Homo sapiens	0-20
27897077-1	2017	Acetylcholinesterase (AChE) is an important enzyme responsible for Alzheimer"s disease, as per report, keto-enol form of curcumin inhibits this enzyme.	keto-enol	103-112	acetylcholinesterase (Cartwright blood group)	Homo sapiens	22-26
22227389-0	2012	Human tRNA(Lys3)(UUU) is pre-structured by natural modifications for cognate and wobble codon binding through keto-enol tautomerism.	keto-enol	110-119	mitochondrially encoded tRNA glycine	Homo sapiens	6-15
20181392-5	2010	The color of a curcumin derivative with keto-enol tautomerism, which was substituted at the C-4 position, changed from yellow to orange within 30 min of being combined with Abeta aggregates in physiological buffer.	keto-enol	40-49	amyloid beta precursor protein	Homo sapiens	173-178
20155960-3	2010	Gn/CBS methods provide a qualitatively different description of tautomeric (keto-enol) equilibrium in 2-substituted acetaldehydes.	keto-enol	76-85	cystathionine beta-synthase	Homo sapiens	3-6
19674910-7	2009	Docking of all HQ(Ph) tautomers on ICAM-1 protein was performed suggesting one keto-enol form favored to act in biological environment.	keto-enol	79-88	intercellular adhesion molecule 1	Homo sapiens	35-41
19932817-0	2009	A liquid chromatography-tandem mass spectrometry confirmatory assay for the simultaneous determination of several tetracyclines in milk considering keto-enol tautomerism and epimerization phenomena.	keto-enol	148-157	Weaning weight-maternal milk	Bos taurus	131-135
9011374-2	1996	Model experiments with chemically synthesized methyl 6-deoxy-4-keto-glucoside (9) revealed that dTDP-6-deoxy-alpha-D-ribo-hexopyran-3-ulose (3) is formed by keto-enol tautomerization during the isolation procedure from initially formed dTDP-6-deoxy-alpha-D-xylo-hexopyran-4-ulose (2).	keto-enol	157-166	TAR DNA-binding protein-43 homolog	Drosophila melanogaster	96-100
15913364-4	2005	Moreover, the halogenated nucleosides shift the tautomeric keto-enol equilibrium strongly toward the keto form, with K(TAUT) [keto]/[enol] approximately 10(4) coming close to that of 2"-deoxyguanosine (10(4)-10(5)), while the nonhalogenated 7-deaza-2"-deoxyisoguanosine 2 shows a K(TAUT) of around 2000 and the enol concentration of 1 is 10% in aqueous solution.	keto-enol	59-68	solute carrier family 6 member 6	Homo sapiens	119-123
15913364-4	2005	Moreover, the halogenated nucleosides shift the tautomeric keto-enol equilibrium strongly toward the keto form, with K(TAUT) [keto]/[enol] approximately 10(4) coming close to that of 2"-deoxyguanosine (10(4)-10(5)), while the nonhalogenated 7-deaza-2"-deoxyisoguanosine 2 shows a K(TAUT) of around 2000 and the enol concentration of 1 is 10% in aqueous solution.	keto-enol	59-68	solute carrier family 6 member 6	Homo sapiens	282-286
15271357-6	2004	Based on this finding, a mechanism of keto-enol tautomerization of GA catalyzed by HSP90 is proposed.	keto-enol	38-47	heat shock protein 90 alpha family class A member 1	Homo sapiens	83-88
9665726-11	1998	The structural and mechanistic parallels place 4-OT, CHMI, and MIF in a superfamily of enzymes related by their ability to catalyze the keto-enol tautomerization of a pyruvyl moiety.	keto-enol	136-145	macrophage migration inhibitory factor	Homo sapiens	63-66
9011374-2	1996	Model experiments with chemically synthesized methyl 6-deoxy-4-keto-glucoside (9) revealed that dTDP-6-deoxy-alpha-D-ribo-hexopyran-3-ulose (3) is formed by keto-enol tautomerization during the isolation procedure from initially formed dTDP-6-deoxy-alpha-D-xylo-hexopyran-4-ulose (2).	keto-enol	157-166	TAR DNA-binding protein-43 homolog	Drosophila melanogaster	236-240
35385201-5	2022	For instance, the acyl moiety is suitable for transesterification reactions in presence of different heteroatom-based nucleophiles ( C -, O -, N -, S -, Se -); these reactions are irreversible thanks to the formation of acetone, obtained upon keto-enol tautomerization of the prop-1-en-2-ol (isopropenyl) leaving group.	keto-enol	243-252	PROP paired-like homeobox 1	Homo sapiens	276-282
33995994-6	2021	There is a subsequent rate-limiting keto-enol tautomerisation step (DeltaG   = 10.5 kcal mol-1) to reach the inactivated BTK/ibrutinib complex.	keto-enol	36-45	Bruton tyrosine kinase	Homo sapiens	121-124
32940040-2	2020	Apart from its cytokine activity, MIF also harbors enzyme activity for keto-enol tautomerization.	keto-enol	71-80	macrophage migration inhibitory factor	Homo sapiens	34-37