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Merck
CN

SML3100

AFMT racemate

≥98% (HPLC), E. faecalis pyridoxal-5′-phosphate-dependent tyrosine decarboxylase inhibitor, powder

Synonym(s):

α-(Fluoromethyl)-D/L-tyrosine, (R/S)-α-Fluoromethyltyrosine, (R/S)-2-Amino-3-fluoro-2-(4-hydroxybenzyl)propanoic acid, Alpha-(FluoroMethyl)-D/L-Tyrosine, D/L-AFMT

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About This Item

Empirical Formula (Hill Notation):
C10H12FNO3
CAS Number:
73804-76-9
Molecular Weight:
213.21
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

AFMT racemate, ≥98% (HPLC)

InChI

1S/C10H12FNO3/c11-6-10(12,9(14)15)5-7-1-3-8(13)4-2-7/h1-4,13H,5-6,12H2,(H,14,15)

InChI key

ACIQAJKTARSFHQ-UHFFFAOYSA-N

SMILES string

OC1=CC=C(C=C1)CC(N)(C(O)=O)CF

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

A racemic mixture of D- and L-AFMT. L-AFMT is reported to selectively inhibt against gut bacteria E. faecalis pyridoxal-5′-phosphate (PLP)-dependent tyrosine decarboxylase (TyrDC)-, but not aromatic amino acid decarboxylase (AADC)-, mediated L-dopa decarboxylation (IC50 = 4.7 μM/cell-free, 1.4 μM/in E. faecalis cultures; 20% human AADC inhibition at 650 μM) via covalent adduct formation with TyrDC co-factor PLP. When co-administered with L-dopa (10 mg/kg) and the AADC inhibitor carbidopa (30 mg/kg) to gnotobiotic mice colonized with E. faecalis, L-AFMT (25 mg/kg) significantly increases L-dopa peak serum concentration.
Covalent inhibtor against L-dopa decarboxylation by gut bacteria E. faecalis tyrosine decarboxylase (TyrDC), but not aromatic amino acid decarboxylase (AADC).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000130324
0000130325
0000126750

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Vayu Maini Rekdal et al.
Science (New York, N.Y.), 364(6445) (2019-06-15)
The human gut microbiota metabolizes the Parkinson's disease medication Levodopa (l-dopa), potentially reducing drug availability and causing side effects. However, the organisms, genes, and enzymes responsible for this activity in patients and their susceptibility to inhibition by host-targeted drugs are

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