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2.1.2.1: glycine hydroxymethyltransferase

This is an abbreviated version!
For detailed information about glycine hydroxymethyltransferase, go to the full flat file.

Word Map on EC 2.1.2.1

Reaction

5,10-methylenetetrahydrofolate
+
glycine
 +
H2O
=
tetrahydrofolate
 +
L-serine

Synonyms

AtSHMT3, bsSHMT, bstSHMT, EC 4.1.2.6, eSHMT, GlyA, GlyA protein, glycine hydroxymethyltransferrase, hSHMT, L-serine hydroxymethyltransferase, mitochondrial serine hydroxymethyltransferase, MJ1597, PvSHMT, Rhg4, serine hydroxymethyl transferase, serine hydroxymethylase hydroxymethyltransferase, serine, serine hydroxymethyltransferase, serine hydroxymethyltransferase 1, serine hydroxymethyltransferase 2, serine hydroxymethyltransferase 2alpha, serine transhydroxymethylase, serine:H4F hydroxymethyltransferase, serine:tetrahydrofolate hydroxymethyltransferase, SHM1, SHM2, SHMT, SHMT-1, SHMT-L, SHMT-S, SHMT08, SHMT1, SHMT2, SHMT2alpha, SHMT3, zcSHMT, zebrafish cytosolic serine hydroxymethyltransferase, zebrafish mitochondiral serine hydroxymethyltransferase, zmSHMT

ECTree

     2 Transferases
         2.1 Transferring one-carbon groups
             2.1.2 Hydroxymethyl-, formyl- and related transferases
                2.1.2.1 glycine hydroxymethyltransferase

Inhibitors

Inhibitors on EC 2.1.2.1 - glycine hydroxymethyltransferase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-methyl 5-[3-(6-amino-5-cyano-4-isopropyl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazol-4-yl)-5-cyanophenyl]thiophene-2-carboxylate
-
-
(4R)-6-amino-4-(5-cyano-3'-fluoro[1,1'-biphenyl]-3-yl)-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
(4R,4S)-5-cyano-4-(3-cyano-5-[5-[((S)-1,3-dicarboxypropyl)-carbamoyl]thiophen-2-yl]phenyl)-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-6-aminium trifluoroacetate
(4S)-6-amino-4-(5-cyano-3'-fluoro[1,1'-biphenyl]-3-yl)-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
1,10-phenanthroline
2,2'-dipyridyl
-
-
2-aminoalanine
-
-
2-aminoisobutyrate
-
-
2-mercaptopropionic acid
-
-
3'-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5'-cyano[1,1'-biphenyl]-3-carboxylic acid
3-Bromopyruvate
isoform SHMT1 is completely inhibited by 3-bromopyruvate; isoform SHMT2 retains a significant fraction of activity with 3-bromopyruvate
4-chloro-L-threonine
5,10-methenyltetrahydrofolate
-
-
5,10-methylene-5,6,7,8-tetrahydrofolic acid
-
-
5,5-dithiobis(2-nitrobenzoic acid)
5-formyltetrahydrofolate
-
can inhibit SHMT in vivo and thereby influence glycine pool size, can accumulate glycine in both wild-type and 5-CHO-THF cycloligase mutant
5-formyltetrahydrofolate monoglutamate
5-methyl-5,6,7,8-tetrahydrofolate
-
-
5-methyltetrahydrofolate monoglutamate
5-Methyltetrahydrofolate triglutamate
5-[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]-N,N-dimethylthiophene-2-carboxamide
5-[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]-N-[3-(diethylamino)propyl]thiophene-2-carboxamide
5-[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylic acid
6-amino-3-methyl-4-[3-(morpholin-4-yl)-5-(trifluoromethyl)phenyl]-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
6-amino-4-(3,5-dichlorophenyl)-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
6-amino-4-(5-cyano-3'-fluoro[1,1'-biphenyl]-3-yl)-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
6-amino-4-[3-cyano-5-(piperazin-1-yl)phenyl]-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitril
-
-
6-amino-4-[3-cyano-5-(piperazin-1-yl)phenyl]-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
-
6-amino-5-cyano-4-[3-cyano-5-(5-[[3-(morpholin-4-ium-4-yl)propyl]carbamoyl]thiophen-2-yl)phenyl]-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-1-ium bis-(trifluoroacetate)
allothreonine
-
-
aminoisobutyrate
-
-
aminopterin
Antibodies to cytosolic enzyme
-
-
-
Antibodies to mitochondrial enzyme
-
no inhibition of cytosolic enzyme
-
benzyl 4-[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]piperazine-1-carboxylate
benzyl 5-[3-[(4R)-6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylate
benzyl 5-[3-[(4S)-6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylate
benzyl 5-[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylate
beta-Alanine
beta-Aminoalanine
-
-
beta-chloroalanine
-
suicide substrate
beta-trifluoroallothreonine
beta-trifluorothreonine
Bromopyruvate
carboxymethoxylamine
-
strong
Chloroacetaldehyde
Cibacron blue F3GA
CO(NH2)2
60.59% residual activity at 1 mM
D-alanine
D-beta-fluoroalanine
D-cycloserine
Dichloromethotrexate
dihydrofolate
-
-
dithiothreitol
59.29% residual activity at 1 mM
DL-2-methylserine
DL-allothreonine
-
-
DL-O-Methylserine
-
-
DTT
strong inhibition
ethyl 4-[[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl](methyl)amino]butanoate
formaldehyde
Glycidaldehyde
glycine
guanidine hydrochloride
86% loss of activity at 0.25 M
iodoacetamide
L-alanine
L-alpha,beta-diaminopropionic acid
-
-
L-amino acids
L-cysteine
L-methionine
L-mimosine
-
inhibits SHMT1 transcription by chelating zinc, eliminates the metal regulatory element- and Sp1-binding activity in nuclear extracts from MCF-7 cells, but not in nuclear extracts from the mimosine-resistant cell line, MCF-7/2a
L-serine
L-threonine
-
-
leucovorin
leucovorin (N5-CHO-THF) exhibits a differential inhibition pattern: it significantly inhibits the aldol cleavage of serine catalyzed by zebrafish cytosolic SHMT but it inhibits to a lesser extent the reaction catalyzed by the mitochondrial isozyme. Approximately 70% and 30% inhibition are observed for zebrafish cytosolic- and zebrafish mitochondrial SHMT activities, respectively, in the presence of 70 mM leucovorin. An even larger difference between both isoenzymes is observed when the inhibition is assayed in the presence of 50 mM serine; leucovorin (N5-CHO-THF) exhibits a differential inhibition pattern: it significantly inhibits the aldol cleavage of serine catalyzed by zebrafish cytosolic SHMT but it inhibits to a lesser extent the reaction catalyzed by the mitochondrial isozyme. Approximately 70% and 30% inhibition are observed for zebrafish cytosolic- and zebrafish mitochondrial SHMT activities, respectively, in the presence of 70 mM leucovorin. An even larger difference between both isoenzymes is observed when the inhibition is assayed in the presence of 50 mM serine
lometrexol
methotrexate
methyl 3'-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5'-chloro[1,1'-biphenyl]-4-carboxylate
methyl 5-[3-[(4R)-6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylate
methyl 5-[3-[(4S)-6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylate
methyl 5-[3-[6-amino-5-cyano-3-methyl-4-(propan-2-yl)-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-5-cyanophenyl]thiophene-2-carboxylate
-
-
methyl methanethiosulfonate
N-ethylmaleimide
-
-
NAD+
-
negative effector
NH2OH
nolatrexed
-
poor inhibition
O-phosphoserine
-
-
pemetrexed
permetrexed
-
-
phenylhydrazine
-
partially reversible by pyridoxal 5'-phosphate
pyrimethamine
-
-
raltitrexed
S-adenosyl-L-methionine
-
-
Sodium borohydride
-
-
substituted hydroxylamine derivates
-
sulfonyl fluoride triazine derivates
tetrahydrofolate
tetrahydrofolate derivatives
-
tetrahydropteroylglutamate
-
Thiosemicarbazide
additional information
-