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SMB00287

Sigma-Aldrich

Formycin A

from Streptomyces kaniharaensis, ≥98% (HPLC)

Synonym(s):
1-C-(7-Amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1,4-anhydro-(1S)-D-Ribitol, NSC 102811, 8-Aza-9-deazaadenosine, 7-Amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidine, Formycin
Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
Molecular Weight:
267.24
Beilstein:
624229
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

biological source

Streptomyces kaniharaensis

assay

≥98% (HPLC)

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

white to off-white

solubility

DMSO: soluble 1 mg/mL
H2O: soluble 3 mg/mL

Mode of action

enzyme | inhibits

antibiotic activity spectrum

viruses (Antiretroviral)

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

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General description

Formycin A is an adenosine analog, and is cytotoxic in nature. It acts as a substrate for the human enzymes human erythrocytic adenosine deaminase and adenosine kinase.
Chemical structure: nucleoside

Biochem/physiol Actions

Formycin A possess antitumor function, along with its antibacterial and antiviral activity.
Formycin A (FA) is a C-nucleoside that inhibits the E.coli enzyme purine nucleoside phosphorylase (PNP). FA was found to upsurge insulin release elevated by glucose, and was also shown to inhibit 5′-Methylthioadenosine/S-adenosylhomocysteine (MTA/AdoHcy) nucleosidase, an enzyme important in the recycling of methionine. Research has shown FA is an antiretroviral agent against HIV-1, targeting reverse transcription.

Packaging

10MG

Other Notes

Store the product sealed at –20 °C. Under these conditions the product is stable for at least 4 years.
Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

More documents

Quotes and Ordering

Michael J Dapp et al.
Journal of virology, 88(1), 354-363 (2013-10-25)
Reverse transcription is an important early step in retrovirus replication and is a key point targeted by evolutionarily conserved host restriction factors (e.g., APOBEC3G, SamHD1). Human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) is a major target of antiretroviral
A Bzowska et al.
Biochimica et biophysica acta, 1120(3), 239-247 (1992-04-17)
Formycin B (FB), a moderate inhibitor (Ki approximately 100 microM) of mammalian purine nucleoside phosphorylase (PNP), and formycin A (FA), which is totally inactive vs. the mammalian enzyme, are both effective inhibitors of the bacterial (Escherichia coli) enzyme (Ki approximately
Helmut Rosemeyer et al.
Chemistry & biodiversity, 16(4), e1900012-e1900012 (2019-02-19)
Two lipophilic derivatives of formycin A (1) and formycin B (5) carrying an O-2',3'-(ethyl levulinate) ketal group have been prepared. These were base-alkylated at N(1) (for 1) and N(1) and N(6) (for 5) with both isopentenyl and all-trans-farnesyl residues. Upon
C-4? Truncated carbocyclic formycin derivatives
Zhou J, et al.
Tetrahedron, 62(29), 7009-7013 (2006)
R P Agarwal et al.
The Journal of clinical investigation, 57(4), 1025-1035 (1976-04-01)
Deficiency of erythrocytic and lymphocytic adenosine deaminase (ADA) occurs in some patients with severe combined immunodeficiency disease (SCID). SCID with ADA deficiency is inherited as an autosomal recessive trait. ADA is markedly reduced or undetectable in affected patients (homozygotes), and

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