Skip to Content
Merck
All Photos(1)

Documents

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, 7-Amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidine, 8-Aza-9-deazaadenosine, Formycin, NSC 102811

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
Molecular Weight:
267.24
Beilstein:
624229
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces kaniharaensis

Quality Level

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

antibiotic activity spectrum

viruses (Antiretroviral)

Mode of action

enzyme | inhibits

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

Looking for similar products? Visit Product Comparison Guide

General description

Chemical structure: nucleoside
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.

Biochem/physiol Actions

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.
Formycin A possess antitumor function, along with its antibacterial and antiviral activity.

Packaging

10MG

Other Notes

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

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


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

C-4? Truncated carbocyclic formycin derivatives
Zhou J, et al.
Tetrahedron, 62(29), 7009-7013 (2006)
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
W J Malaisse et al.
Biochemical and molecular medicine, 57(1), 47-63 (1996-02-01)
Formycin A augments insulin release evoked by glucose (5.6 mm or more), this effect not being rapidly reversible. The mechanism responsible for the insulinotropic action of formycin A was investigated in isolated pancreatic islets. It could not be ascribed to
Meng Zhang et al.
Applied and environmental microbiology, 86(2) (2019-11-05)
Formycin A (FOR-A) and pyrazofurin A (PRF-A) are purine-related C-nucleoside antibiotics in which ribose and a pyrazole-derived base are linked by a C-glycosidic bond. However, the logic underlying the biosynthesis of these molecules has remained largely unexplored. Here, we report
Jeffrey E Lee et al.
The Journal of biological chemistry, 278(10), 8761-8770 (2002-12-24)
5'-Methylthioadenosine/S-adenosylhomocysteine (MTA/AdoHcy) nucleosidase is a key enzyme in a number of critical biological processes in many microbes. This nucleosidase catalyzes the irreversible hydrolysis of the N(9)-C(1') bond of MTA or AdoHcy to form adenine and the corresponding thioribose. The key

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service