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Key Documents

SMB00939

Sigma-Aldrich

1-Methyladenosine

≥95% (HPLC)

Synonym(s):

1-Methyladenosine, N1-Methyladenosine

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About This Item

Empirical Formula (Hill Notation):
C11H15N5O4
CAS Number:
Molecular Weight:
281.27
MDL number:
UNSPSC Code:
12352123
NACRES:
NA.79

Quality Level

Assay

≥95% (HPLC)

form

solid

color

white

storage temp.

-10 to -25°C

SMILES string

CN1C=Nc2c(ncn2[C@@H]3O[C@@H](CO)[C@H](O)[C@@H]3O)C1=N

InChI

1S/C11H15N5O4/c1-15-3-14-10-6(9(15)12)13-4-16(10)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11-12,17-19H,2H2,1H3/t5-,7-,8-,11-/m1/s1

InChI key

GFYLSDSUCHVORB-IOSLPCCCSA-N

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General description

1-Methyladenosine is an RNA modification that arises through distinct processes, including enzymatic catalysis and the alkylation of RNA by specific agents.
1-Methyladenosine, also known as M1A, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. 1-Methyladenosine is a strong basic compound (based on its pKa). Precise m6A mapping by m6A-CLIP/IP (briefly m6A-CLIP) revealed that a majority of m6A locates in the last exon of mRNAs in multiple tissues/cultured cells of mouse and human, and the m6A enrichment around stop codons is a coincidence that many stop codons locate round the start of last exons where m6A is truly enriched. The methylation of adenosine is directed by a large m6A methyltransferase complex containing METTL3 as the SAM-binding sub-unit. Insulin-like growth factor-2 mRNA-binding proteins 1, 2, and 3 (IGF2BP1–3) are reported as a novel class of m6A readers.

Application

1-Methyladenosine, a modified nucleoside produced during tRNA processing by methyltransferases, has garnered attention as a potential biomarker for early cancer detection due to its elevated urinary excretion in various cancer forms. Additionally, its presence can be monitored in serum. Moreover, 1-Methyladenosine levels rise during active rheumatoid arthritis, making it a promising indicator for this condition. It finds application in research pertaining to cancer, autoimmune diseases, metabolomics, biomarker discovery and drug discovery studies.

Other Notes

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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