eritadenine
{{Chembox
| ImageFile = Eritadenine.svg
| ImageSize = 150px
| ImageAlt =
| PIN = (2R,3R)-4-(6-Amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid
| OtherNames = Lentysine; Lentinacin
|Section1={{Chembox Identifiers
| CASNo = 23918-98-1
| PubChem = 159961
| ChemSpiderID = 140628
| UNII = 41T27K4B9F
| SMILES = c1nc(c2c(n1)n(cn2)C[C@H]([C@H](C(=O)O)O)O)N
| InChI = 1/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1
| InChIKey = LIEMBEWXEZJEEZ-INEUFUBQBZ
| StdInChI = 1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1
| StdInChIKey = LIEMBEWXEZJEEZ-INEUFUBQSA-N }}
|Section2={{Chembox Properties
| C=9|H=11|N=5|O=4
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Eritadenine is a chemical compound found in shiitake mushrooms. Eritadenine is an inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH) and has hypocholesterolemic activity.{{Cite web|url=https://drugs.ncats.io/drug/41T27K4B9F|title=NCATS Inxight: Drugs — ERITADENINE|website=drugs.ncats.io|language=en|access-date=2020-01-22}}
Synthesis
The structure is a purine alkylated with an oxidized sugar fragment.
File:Eritadenine synthesis.svg
Ring opening of the protected lactone (1), derived from erythrose with sodium phthalimide gives the acid 2; hydrazinolysis (cf Gabriel synthesis) then leads to the amino acid 3. Displacement of chlorine in pyrimidine 4 by the amine function on 3 serves to attach the future imidazole nitrogen and the sugar-derived sidechain (5). The nitro group is then reduced by catalytic hydrogenation, the resulting primary amine is the most basic and is selectively formylated with formic acid. These strongly acidic conditions serve to remove the acetonide protecting group as well (6). Treatment with NaOH then serves to close the imidazole ring, forming eritadenine (7)
References
{{Reflist}}
External links
- [https://www.ncbi.nlm.nih.gov/pubmed/17214973 Structure and function of eritadenine and its 3-deaza analogues]