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73156

Sigma-Aldrich

N-Methyl-L-serine

≥98% (TLC)

Synonym(s):

(S)-3-Hydroxy-2-(methylamino)propionic acid, N-Me-Ser-OH

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About This Item

Empirical Formula (Hill Notation):
C4H9NO3
CAS Number:
2480-26-4
Molecular Weight:
119.12
Beilstein:
2498641
MDL number:
MFCD00037756
UNSPSC Code:
12352202
PubChem Substance ID:
329764666
NACRES:
NA.32

Assay

≥98% (TLC)

form

powder

optical activity

[α]/D +9.5±1.0°, c = 1 in 1 M HCl

composition

carbon, 39.5-41.1%
nitrogen, 11.5-12.0%

color

white

mp

204 °C

SMILES string

CN[C@@H](CO)C(O)=O

InChI

1S/C4H9NO3/c1-5-3(2-6)4(7)8/h3,5-6H,2H2,1H3,(H,7,8)/t3-/m0/s1

InChI key

PSFABYLDRXJYID-VKHMYHEASA-N

Biochem/physiol Actions

N-Methyl amino acids play an important role in investigations on prevention or therapy of Alzheimer′s disease, neurofibrillary tangles or amyloid plaque are physiological characteristics of this disease and ?-amyloid(40) fibrillogenesis and disassembly of ?-amyloid(40) fibrils is inhibited by short ?-amyloid congeners containing N-methyl amino acids at alternate residue. N-Methyl-L-serine stimulates hyaluronan production in human skin fibroblasts.
N-Methyl-L-serine has been found to stimulate production of high molecular mass hyaluronan in human fibroblasts. This effect was specific to methylated L-serine and not observed with other methylated amino acids.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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N-Methyl-L-serine stimulates hyaluronan production in human skin fibroblasts.
Sakai, S., et al.
Skin Pharmacology and Physiology, 12, 276-283 (1999)
Péter Nemes et al.
Journal of mass spectrometry : JMS, 40(1), 43-49 (2004-12-08)
The association properties of natural and non-natural amino acids were studied in detail using electrospray ionization mass spectrometry. The results show a highly diverse cluster formation behavior of amino acids. There are differences regarding the degree of clustering (average cluster
D J Gordon et al.
Biochemistry, 40(28), 8237-8245 (2001-07-11)
A potential goal in the prevention or therapy of Alzheimer's disease is to decrease or eliminate neuritic plaques composed of fibrillar beta-amyloid (Abeta). In this paper we describe N-methyl amino acid containing congeners of the hydrophobic "core domain" of Abeta

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