MedKoo Cat#: 407451 | Name: Erythrofuranosyladenine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Erythrofuranosyladenine, also known as 9-beta-D-Erythrofuranosyladenine and ETA, is a nontoxic MTAP substrate. Erythrofuranosyladenine is an effective salvage agent for methylthioadenosine phosphorylase–selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine. The cytotoxicity of EFA to hematopoietic progenitors erythroid burst-forming units (BFU-Es) and granulocyte-macrophage colony-forming units (CFU-GMs) was at least 26- to 41-fold less than that of MTA. EFA selectively rescued MTAP+ MOLT-4 cells from L-alanosine toxicity at 25 microM with negligible toxicity even at 100 microM. EFA is an effective agent for salvaging MTAP+ cells from L-alanosine toxicity and is superior to MTA due to lower cytotoxicity.

Chemical Structure

Erythrofuranosyladenine
Erythrofuranosyladenine
CAS#17019-46-4

Theoretical Analysis

MedKoo Cat#: 407451

Name: Erythrofuranosyladenine

CAS#: 17019-46-4

Chemical Formula: C9H11N5O3

Exact Mass: 237.0862

Molecular Weight: 237.22

Elemental Analysis: C, 45.57; H, 4.67; N, 29.52; O, 20.23

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Erythrofuranosyladenine, 9-beta-D-Erythrofuranosyladenine, 9-β-D-Erythrofuranosyladenine, ETA.
IUPAC/Chemical Name
(2R,3R,4R)-2-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diol
InChi Key
DTGVOXMKTYPSSO-NVMQTXNBSA-N
InChi Code
InChI=1S/C9H11N5O3/c10-7-5-8(12-2-11-7)14(3-13-5)9-6(16)4(15)1-17-9/h2-4,6,9,15-16H,1H2,(H2,10,11,12)/t4-,6-,9-/m1/s1
SMILES Code
NC1=C2C(N([C@H]3[C@@H]([C@@H](CO3)O)O)C=N2)=NC=N1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 237.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Batova A, Cottam H, Yu J, Diccianni MB, Carrera CJ, Yu AL. EFA (9-beta-D-erythrofuranosyladenine) is an effective salvage agent for methylthioadenosine phosphorylase-selective therapy of T-cell acute lymphoblastic leukemia with L-alanosine. Blood. 2006 Feb 1;107(3):898-903. Epub 2005 Oct 18. PubMed PMID: 16234352; PubMed Central PMCID: PMC1895892. 2: Lerner LM. Preparation of nucleosides via isopropylidene sugar derivatives. IV. Synthesis of 9-alpha and 9-beta-L-erythrofuranosyladenine. J Org Chem. 1969 Jan;34(1):101-3. PubMed PMID: 5768222. 3: Marcé S, Balagué O, Colomo L, Martinez A, Höller S, Villamor N, Bosch F, Ott G, Rosenwald A, Leoni L, Esteller M, Fraga MF, Montserrat E, Colomer D, Campo E. Lack of methylthioadenosine phosphorylase expression in mantle cell lymphoma is associated with shorter survival: implications for a potential targeted therapy. Clin Cancer Res. 2006 Jun 15;12(12):3754-61. PubMed PMID: 16778103.