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SMB01333

Sigma-Aldrich

Acetyl-6-formylpterin

≥95% (HPLC)

Sinónimos:

2-Acetamido-4-oxopteridine-6-carboxaldehyde, 2-Acetamido-6-formylpteridin-4(3H)-one, 2-Acetylamino-4-hydroxy-6-formylpteridine, 2-Acetamido-6-formylpteridin-4-one, N-(6-formyl-4-hydroxy-2-pteridinyl)acetamide, N-(6-formyl-4-oxo-1H-pteridin-2-yl)acetamide

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About This Item

Fórmula empírica (notación de Hill):
C9H7N5O3
Número de CAS:
29769-49-1
Peso molecular:
233.18
MDL number:
MFCD28368502
UNSPSC Code:
12352205
NACRES:
NA.77

Quality Level

100

assay

≥95% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CC(=O)NC1=NC2=NC=C(N=C2C(=O)N1)C=O

InChI

1S/C9H7N5O3/c1-4(16)11-9-13-7-6(8(17)14-9)12-5(3-15)2-10-7/h2-3H,1H3,(H2,10,11,13,14,16,17)

InChI key

DDBCPKAHJKOGKK-UHFFFAOYSA-N

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General description

Acetyl-6-formylpterin is a vitamin B9 (folate) metabolite and ligand to MHC class I-related protein 1 (MR1) antigens presented on mucosal-associated invariant T (MAIT) cells.
Acetyl-6-formylpterin, also known as 2-Acetamido-6-formylpteridin-4-one, is a pteridine derivative and a reductive amination product derived from folic acid. This unique compound undergoes a reductive amination reaction, generating formyl groups that can be subsequently acetylated or alkylated, resulting in the formation of stable compounds with diverse properties. Current research highlights the multifaceted nature of this compound, indicating its potential biological activities, including neuroprotective, antitumor, and anticancer properties.

Moreover, acetyl-6-formylpterin serves as a precursor in the synthesis of 2′-hydroxy-7,8-dihydrofolate, a metabolite associated with para-aminosalicylic acid (PAS) in M. tuberculosis. This compound′s versatility and involvement in various biological processes make it an intriguing molecule for metabolomics and biochemical research.

Application

Acetyl-6-formylpterin has been used:
  • to study the potential reversal of iver fibrosis
  • in metabolomics research

Biochem/physiol Actions

Acetyl-6-formylpterin is involved in the enzymatic conversion of GTP to BH4, playing a role in the regulation of neurotransmitter synthesis and other biological processes.

Features and Benefits

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number

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Hamish E G McWilliam et al.
Nature immunology, 17(5), 531-537 (2016-04-05)
The antigen-presenting molecule MR1 presents vitamin B-related antigens (VitB antigens) to mucosal-associated invariant T (MAIT) cells through an uncharacterized pathway. We show that MR1, unlike other antigen-presenting molecules, does not constitutively present self-ligands. In the steady state it accumulates in
Lars Kjer-Nielsen et al.
Nature, 491(7426), 717-723 (2012-10-12)
Antigen-presenting molecules, encoded by the major histocompatibility complex (MHC) and CD1 family, bind peptide- and lipid-based antigens, respectively, for recognition by T cells. Mucosal-associated invariant T (MAIT) cells are an abundant population of innate-like T cells in humans that are
Morgane Mabire et al.
Nature communications, 14(1), 1830-1830 (2023-04-04)
Recent data have shown that liver fibrosis can regress even at later stages of cirrhosis and shifting the immune response from pro-inflammatory towards a resolutive profile is considered as a promising option. The immune regulatory networks that govern the shift
Sidonia B G Eckle et al.
The Journal of experimental medicine, 211(8), 1585-1600 (2014-07-23)
Mucosal-associated invariant T (MAIT) cells express an invariant T cell receptor (TCR) α-chain (TRAV1-2 joined to TRAJ33, TRAJ20, or TRAJ12 in humans), which pairs with an array of TCR β-chains. MAIT TCRs can bind folate- and riboflavin-based metabolites restricted by

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