N-Methyl-D-serine

N-Methyl-D-serine

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N-Methyl-D-serine
Category Others
Catalog number BBF-05241
CAS 915405-01-5
Molecular Weight 119.12
Molecular Formula C4H9NO3
Purity >95% by HPLC

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Specification

Related CAS 2480-26-4 (L-configuration)
Synonyms Me-D-Ser-OH; (R)-3-Hydroxy-2-(methylamino)propanoic acid; D-Serine, N-Methyl-; methyl-D-serine
Storage Store at -20°C
IUPAC Name (2R)-3-hydroxy-2-(methylamino)propanoic acid
Canonical SMILES CNC(CO)C(=O)O
InChI InChI=1S/C4H9NO3/c1-5-3(2-6)4(7)8/h3,5-6H,2H2,1H3,(H,7,8)/t3-/m1/s1
InChI Key PSFABYLDRXJYID-GSVOUGTGSA-N

Properties

Appearance Solid
Boiling Point 326.2±32.0°C at 760 mmHg
Density 1.242 g/cm3

Reference Reading

1. N-Methyl-L-serine stimulates hyaluronan production in human skin fibroblasts
S Sakai, T Sayo, S Kodama, S Inoue Skin Pharmacol Appl Skin Physiol. 1999 Sep-Oct;12(5):276-83. doi: 10.1159/000066253.
We examined the effects of N-methyl-L-serine (NMS), an amino acid derivative, on hyaluronan (HA) synthesis in human skin fibroblasts. NMS (1-10 mM), but not L-serine, stimulated the incorporation of [(3)H]glucosamine into HA dose-dependently, with a maximum stimulation of 1.5-fold compared to the control. The effect of NMS was specific for HA production, because there was no change in sulfated glycosaminoglycan formation. Neither the N-methyl derivatives of L-glycine or L-alanine, nor N-methyl-D-serine, could stimulate HA synthesis, indicating that the beta-hydroxyl group and the L-configuration were essential for the activity. Gel filtration of the products showed that NMS stimulated the production of high-molecular-mass HA (>10(6) D) without affecting the production of low-molecular-mass HA. NMS required 24 h to stimulate HA production, and when fibroblasts were pretreated for 10-24 h with NMS (1-10 mM), membrane-associated HA synthase activity was increased dose-dependently. Thus, a second messenger is likely to be involved in the stimulation of HA production by NMS.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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