Eritadenine: Difference between revisions

Eritadenine
Names
	IUPAC name (2R,3R)-4-(6-Aminopurin-9-yl)-2,3-dihydroxybutanoic acid
	Other names Lentysine; Lentinacin
Identifiers
CAS Number	23918-98-1;
3D model (JSmol)	Interactive image;
ChemSpider	140628;
PubChem CID	159961;
UNII	41T27K4B9F;
CompTox Dashboard (EPA)	DTXSID00178632 ;
	InChI InChI=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 Key: LIEMBEWXEZJEEZ-INEUFUBQSA-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 Key: LIEMBEWXEZJEEZ-INEUFUBQBZ;
	SMILES c1nc(c2c(n1)n(cn2)C[C@H]([C@H](C(=O)O)O)O)N;
Properties
Chemical formula	C9H11N5O4
Molar mass	253.218 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Revision as of 22:49, 18 June 2019

Eritadenine is a chemical compound found in shiitake mushrooms. Eritadenine is an inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH) and has hypocholesterolemic activity.^{[citation needed]}

Synthesis

The structure is a purine alkylated with an oxidized sugar fragment.

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

^ Kamiya, T.; Saito, Y.; Hashimoto, M.; Seki, H. (1969). "Structure and synthesis of lentysine, a new hypocholesterolemic substance". Tetrahedron Letters. 10 (53): 4729–4732. doi:10.1016/S0040-4039(01)88795-5.
^ Kamiya, T.; Saito, Y.; Hashimoto, M.; Seki, H. (1972). "Hypocholesterolemic alkaloids of lentinus edodes (berk.) sing. II. A novel synthesis of eritadenine". Journal of Heterocyclic Chemistry. 9 (2): 359–362. doi:10.1002/jhet.5570090230.

External links

Structure and function of eritadenine and its 3-deaza analogues

[1] Kamiya, T.; Saito, Y.; Hashimoto, M.; Seki, H. (1969). "Structure and synthesis of lentysine, a new hypocholesterolemic substance". Tetrahedron Letters. 10 (53): 4729–4732. doi:10.1016/S0040-4039(01)88795-5.

[2] Kamiya, T.; Saito, Y.; Hashimoto, M.; Seki, H. (1972). "Hypocholesterolemic alkaloids of lentinus edodes (berk.) sing. II. A novel synthesis of eritadenine". Journal of Heterocyclic Chemistry. 9 (2): 359–362. doi:10.1002/jhet.5570090230.

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[2]

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 }}
-'''Eritadenine''' is an isolate of [[Shiitake]]. Eritadenine is an inhibitor of [[S-adenosyl-L-homocysteine hydrolase]] (SAHH) and has hypocholesterolemic activity.
+'''Eritadenine''' is a chemical compound found in [[shiitake]] mushrooms. Eritadenine is an inhibitor of [[S-adenosyl-L-homocysteine hydrolase]] (SAHH) and has hypocholesterolemic activity.{{cn}}
 ==Synthesis==
 The structure is a purine alkylated with an oxidized sugar fragment.
-[[File:Eritadenine synthesis.svg|thumb|center|700px|Eritadenine synthesis:<ref>{{cite journal | doi=10.1016/S0040-4039(01)88795-5 }}</ref> Alternative synthesis:<ref>{{cite journal | doi=10.1002/jhet.5570090230 }}</ref>]]
+[[File:Eritadenine synthesis.svg|thumb|center|700px|Eritadenine synthesis:<ref>{{cite journal | doi=10.1016/S0040-4039(01)88795-5 | title=Structure and synthesis of lentysine, a new hypocholesterolemic substance | journal=Tetrahedron Letters | volume=10 | issue=53 | pages=4729–4732 | year=1969 | last1=Kamiya | first1=T. | last2=Saito | first2=Y. | last3=Hashimoto | first3=M. | last4=Seki | first4=H. }}</ref> Alternative synthesis:<ref>{{cite journal | doi=10.1002/jhet.5570090230 | title=Hypocholesterolemic alkaloids of lentinus edodes (berk.) sing. II. A novel synthesis of eritadenine | journal=Journal of Heterocyclic Chemistry | volume=9 | issue=2 | pages=359–362 | year=1972 | last1=Kamiya | first1=T. | last2=Saito | first2=Y. | last3=Hashimoto | first3=M. | last4=Seki | first4=H. }}</ref>]]
 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''')
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 * [https://www.ncbi.nlm.nih.gov/pubmed/17214973 Structure and function of eritadenine and its 3-deaza analogues]
-[[Category:Edible fungi]]
+[[Category:Alkaloids]]
-[[Category:Organic chemistry]]
+[[Category:Carboxylic acids]]
-{{organic-chem-stub}}