H-2-Me-D-Ser-OH
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H-2-Me-D-Ser-OH

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Category
DL-Amino Acids
Catalog number
BAT-008895
CAS number
81132-44-7
Molecular Formula
C4H9NO3
Molecular Weight
119.12
H-2-Me-D-Ser-OH
IUPAC Name
(2R)-2-amino-3-hydroxy-2-methylpropanoic acid
Synonyms
H-D-aMeSer-OH; 2-Methyl-D-serine; H-alpha-Me-D-Ser-OH; H alpha Me D Ser OH; H 2 Me D Ser OH
Appearance
Off-white solid
Purity
98%
Density
1.3±0.1 g/cm3
Melting Point
286-288ºC
Boiling Point
345.8±32.0 °C at 760 mmHg
Application
A potential chiral building blocks for the synthesis of different α -methyl α -amino acids.
InChI
InChI=1S/C4H9NO3/c1-4(5,2-6)3(7)8/h6H,2,5H2,1H3,(H,7,8)/t4-/m1/s1
InChI Key
CDUUKBXTEOFITR-SCSAIBSYSA-N
Canonical SMILES
CC(CO)(C(=O)O)N
1.3,1-Benzothiazines, 1,4-Benzodioxines and 1,4-Benzoxazines as Inhibitors of Matriptase-2: Outcome of a Focused Screening Approach.
Roydeva PG1, Beckmann AM2, Stirnberg M3, Cesar J4, Kikelj D5, Ilaš J6, Gütschow M7. Pharmaceuticals (Basel). 2016 Jan 13;9(1). pii: E2. doi: 10.3390/ph9010002.
The liver enzyme matriptase-2 is a multi-domain, transmembrane serine protease with an extracellular, C-terminal catalytic domain. Synthetic low-molecular weight inhibitors of matriptase-2 have potential as therapeutics to treat iron overload syndromes, in particular in patients with β-thalassemia. A sub-library of 64 compounds was screened for matriptase-2 inhibition and several active compounds were identified. (S)-Ethyl 2-(benzyl(3-((4-carbamidoylphenoxy)methyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-2-oxoacetate ((S)-12) showed an IC50 value of less than 10 µM. Structure-activity relationships were discussed and proposals to design new matriptase-2 inhibitors were made.
2.Determination of D-serine in human serum by LC-MS/MS using a triazole-bonded column after pre-column derivatization with (S)-4-(3-isothiocyanatopyrrolidin-1-yl)-7- (N, N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole.
Sakamoto T1, Kuwabara R1, Takahashi S1, Onozato M1, Ichiba H1, Iizuka H1, Fukushima T2. Anal Bioanal Chem. 2016 Jan;408(2):517-26. doi: 10.1007/s00216-015-9119-y. Epub 2015 Nov 5.
An LC-MS/MS-based method for determining D-serine (Ser), an endogenous co-agonist of the N-methyl-D-aspartate receptor, in human serum, was developed and validated using a triazole-bonded silica-packed column after pre-column fluorescence derivatization with a chiral labeling reagent, (S)-4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole. Enantiomeric separation of the D- and L-Ser derivatives occurred in the triazole-bonded column (R s: 1.85) with CH3CN/100 mM HCO2NH4 in H2O (95.5:4.5) as the mobile phase with isocratic elution. The ln(capacity factor of D-Ser) in the van't Hoff plot gradually decreased with the inverse of temperature, suggesting enhanced hydrophilic interactions with the triazole-bonded stationary phase with increasing column temperature, owing to decrease in the partition coefficient to the mobile phase. Multiple reaction monitoring (m/z 457.10 > 409.00) by triple quadrupole mass spectrometry was used for quantifying D-Ser in human serum.
3.Tideglusib protects neural stem cells against NMDA receptor overactivation.
Armagan G1, Keser A2, Atalayın Ç3, Dagcı T2. Pharmacol Rep. 2015 Oct;67(5):823-31. doi: 10.1016/j.pharep.2015.01.007. Epub 2015 Jan 23.
BACKGROUND: N-methyl-d-aspartate (NMDA) receptors are major pharmacological targets to prevent or reduce the progression of neurodegenerative diseases. Successful therapy with NMDA receptor antagonists in humans has been limited by the severe side effects of complete receptor blockade. The aim of the present study was to investigate the possible protective effects of tideglusib against NMDA receptor overactivation in neural stem cells.
4.Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities.
Kil YS1, Choi SK1, Lee YS1, Jafari M2, Seo EK1. J Nat Prod. 2015 Oct 23;78(10):2481-7. doi: 10.1021/acs.jnatprod.5b00633. Epub 2015 Oct 2.
Five new chalcones, 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1), (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2), 4,2',4'-trihydroxy-3'-[(2E)-3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3), 2',3'-furano-4-hydroxy-4'-methoxychalcone (4), and (±)-4-hydroxy-2',3'-(2,3-dihydro-2-methoxyfurano)-4'-methoxychalcone (5), were isolated from the aerial parts of Angelica keiskei Koidzumi together with eight known chalcones, 6-13, which were identified as (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6), xanthoangelol (7), xanthoangelol F (8), xanthoangelol G (9), 4-hydroxyderricin (10), xanthoangelol D (11), xanthoangelol E (12), and xanthoangelol H (13), respectively. Chalcones 1-13 were evaluated for their promoter activity on heat shock protein 25 (hsp25, murine form of human hsp27). Compounds 1 and 6 activated the hsp25 promoter by 21.
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