PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
6131974-2	1983	Results of glucose tolerance tests in fasted alloxan diabetic rabbits showed that after oral administration of glucose, insulin suppositories containing enamines derived from either sodium phenylalanine or leucine were able to lower the serum glucose level to within the normal range for more than 2.5 h. The absorption-promoting effect of the sodium DL-phenylalanate enamine on rectal absorption of insulin in dogs was studied in two different formulations, gelatin microenema and suppository.	enamines	153-161	insulin	Oryctolagus cuniculus	120-127
6131974-2	1983	Results of glucose tolerance tests in fasted alloxan diabetic rabbits showed that after oral administration of glucose, insulin suppositories containing enamines derived from either sodium phenylalanine or leucine were able to lower the serum glucose level to within the normal range for more than 2.5 h. The absorption-promoting effect of the sodium DL-phenylalanate enamine on rectal absorption of insulin in dogs was studied in two different formulations, gelatin microenema and suppository.	enamines	153-161	insulin	Canis lupus familiaris	400-407
31103411-0	2019	Reactive Enamines and Imines In Vivo: Lessons from the RidA Paradigm.	enamines	9-17	reactive intermediate imine deaminase A homolog	Homo sapiens	55-59
31103411-4	2019	Genetic and biochemical studies have outlined a role for the broadly conserved reactive intermediate deaminase (Rid) (YjgF/YER057c/UK114) protein family, in particular RidA, in catalyzing the hydrolysis of enamines and imines to their ketone product.	enamines	206-214	reactive intermediate imine deaminase A homolog	Homo sapiens	168-172
25010511-1	2014	Stereoselective palladium-catalyzed oxidative C-N bond coupling reactions between aromatic amines and alkenes involving a solvent-controlled regioselective bromination process under 1 atm of oxygen atmosphere are disclosed, providing easy access to two different brominated enamines.	enamines	274-282	ATM serine/threonine kinase	Homo sapiens	184-187
25534147-1	2015	Treatment of diazo vinyl phosphonate with alcohols, amines, and thiols in the presence of Rh(II) results in the chemo- and stereoselective generation of enol ethers, enamines and vinyl sulfides via an X-H insertion process.	enamines	166-174	Rh blood group D antigen	Homo sapiens	90-96
15575681-1	2004	[reaction: see text] Generation of difluorocarbene(carbenoid) in the presence of enamines derived from cyclic ketones results in overall insertion of CF2 to produce bicyclic difluorocyclopropylamines.	enamines	81-89	ATPase H+ transporting accessory protein 1	Homo sapiens	150-153
25070638-6	2014	The purified proteins hydrolyzed the enamines/imines formed by Thr dehydratase from Ser or Thr and protected the Arabidopsis plastidial branched-chain aminotransferase BCAT3 from inactivation by the Ser-derived enamine/imine.	enamines	37-45	branched-chain aminotransferase 3	Arabidopsis thaliana	168-173
21126099-0	2011	Reversal of diastereoselectivity in reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines: metal-free, complementary anti- and syn-selective synthesis of 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones.	enamines	97-105	synemin	Homo sapiens	154-157
20737087-1	2010	Microwave irradiation of chloroacetylarenes and enamines induced an aza-Darzens reaction followed by rearrangement of the aziridinium intermediate to give (2-amino-3-alkenoyl)arenes that were reduced selectively to syn-beta-aminoalcohols as pseudo-ephedrine analogues.	enamines	48-56	synemin	Homo sapiens	215-218
16458517-1	2006	1,4,9,10-Anthradiquinone 5 was reacted with enamines 6 in the Nenitzescu reaction to yield unexpected 3,3a,6,12-tetrahydro-3a,7-dihydroxy-2-methyl-6,12-dioxo-naphtho[2,3-d]indol-1-carboxylates 8A.	enamines	44-52	indoleamine 2,3-dioxygenase 2	Homo sapiens	172-179
20606338-5	2010	These results represent evidence of tautomerism of 5-methyl-2,3-dihydropyrazines (imine forms) to the latent enamine tautomers, and suggest that DHPs may behave as enamines to a significant degree under physiological conditions.	enamines	164-172	deoxyhypusine synthase	Homo sapiens	145-149
34549232-1	2021	A new two-step one-pot aminobromination/chlorination of carbonyl alkynes has been achieved via a Michael addition of aliphatic secondary amines and subsequent beta-bromination/chlorination of the obtained enamines to afford various alpha-X (X = Br or Cl) enamino ketones/esters in moderate to good yields.	enamines	205-213	chromosome 12 open reading frame 73	Homo sapiens	245-247
15453768-5	2004	The experimental results were interpreted on the ground of DFT calculations of the C-Halpha BDE in the starting allylic amines, and of the C-Hgamma BDE in the resulting enamines.	enamines	169-177	homeobox D13	Homo sapiens	148-151
11950357-1	2002	Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) afford readily separated mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones.	enamines	13-21	loss of heterozygosity, 19, chromosomal region 1	Homo sapiens	197-200
12236751-1	2002	The structure and stereodynamics of N,N-bis(silyloxy)enamines (1), a new class of enamines with extraordinary reactivity, have been simulated by the DFT PBE/TZP method.	enamines	53-61	PHD finger protein 20	Homo sapiens	157-160