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Literature DB >> 23635003

Acremolin from Acremonium strictum is N(2),3-etheno-2'-isopropyl-1-methylguanine, not a 1H-azirine. Synthesis and structural revision.

Abstract

The first synthesis of the heterocyclic marine natural product, acremolin, is reported along with the revision of the structure from a 1H-azirine to a substituted N(2),3-ethenoguanine (5-methyl-7-isopropyl-4,5-dihydroimidazo[2,1-b]purine). Additional properties of acremolin are also described including its (1)H-(15)N-HMBC and fluorescence spectra.

Entities: CellLine Chemical Disease Species

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Year: 2013 PMID： 23635003 PMCID： PMC3957326 DOI： 10.1021/ol400752s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

15 in total

1. Etheno adducts formed in DNA of vinyl chloride-exposed rats are highly persistent in liver.

Authors: J A Swenberg; N Fedtke; F Ciroussel; A Barbin; H Bartsch
Journal: Carcinogenesis Date: 1992-04 Impact factor: 4.944

2. 1,N2-ethenoguanine and N2,3-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases.

Authors: P D Sattsangi; N J Leonard; C R Frihart
Journal: J Org Chem Date: 1977-09-30 Impact factor: 4.354

3. Mukaiyama aldol addition to alpha-chloro-substituted aldehydes. Origin of the unexpected syn selectivity.

Authors: Tessie Borg; Jakob Danielsson; Peter Somfai
Journal: Chem Commun (Camb) Date: 2010-01-07 Impact factor: 6.222

4. A general and convenient synthesis of 7-alkyladenines from adenine by regioselective alkylation utilizing blocking/deblocking at the 3-position.

Authors: N J Leonard; T Fujii; T Saito
Journal: Chem Pharm Bull (Tokyo) Date: 1986-05 Impact factor: 1.645

Review 5. Etheno-substituted nucleotides and coenzymes: fluorescence and biological activity.

Authors: N J Leonard
Journal: CRC Crit Rev Biochem Date: 1984

6. A new heterocyclic ring system, 8-acetonyl-4-oxo-4,5-dihydroimidazo[2,1-b]purine, resulting from the reaction of guanine and deoxyribose.

Authors: F B Howard; C A Dekker
Journal: Biochemistry Date: 1967-11 Impact factor: 3.162

7. 15N nuclear magnetic resonance studies on the tautomerism of 8-hydroxy-2'-deoxyguanosine, 8-hydroxyguanosine, and other C8-substituted guanine nucleosides.

Authors: B P Cho; F F Kadlubar; S J Culp; F E Evans
Journal: Chem Res Toxicol Date: 1990 Sep-Oct Impact factor: 3.739

8. Mechanism of formation of ethenoguanine adducts from 2-haloacetaldehydes: 13C-labeling patterns with 2-bromoacetaldehyde.

Authors: F P Guengerich; M Persmark
Journal: Chem Res Toxicol Date: 1994 Mar-Apr Impact factor: 3.739

5. Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems.

Authors: Alexander F Khlebnikov; Mikhail S Novikov; Viktoriia V Pakalnis; Roman O Iakovenko; Dmitry S Yufit
Journal: Beilstein J Org Chem Date: 2014-04-04 Impact factor: 2.883

5 in total

Acremolin from Acremonium strictum is N(2),3-etheno-2'-isopropyl-1-methylguanine, not a 1H-azirine. Synthesis and structural revision.

1. Etheno adducts formed in DNA of vinyl chloride-exposed rats are highly persistent in liver.

2. 1,N2-ethenoguanine and N2,3-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases.

3. Mukaiyama aldol addition to alpha-chloro-substituted aldehydes. Origin of the unexpected syn selectivity.

4. A general and convenient synthesis of 7-alkyladenines from adenine by regioselective alkylation utilizing blocking/deblocking at the 3-position.

Review 5. Etheno-substituted nucleotides and coenzymes: fluorescence and biological activity.

6. A new heterocyclic ring system, 8-acetonyl-4-oxo-4,5-dihydroimidazo[2,1-b]purine, resulting from the reaction of guanine and deoxyribose.

7. 15N nuclear magnetic resonance studies on the tautomerism of 8-hydroxy-2'-deoxyguanosine, 8-hydroxyguanosine, and other C8-substituted guanine nucleosides.

8. Mechanism of formation of ethenoguanine adducts from 2-haloacetaldehydes: 13C-labeling patterns with 2-bromoacetaldehyde.

9. Long-chain 2H-azirines with heterogeneous terminal halogenation from the marine sponge Dysidea fragilis.

10. New azacyclopropene derivatives from Dysidea fragilis collected in Pohnpei.

1. Sydoxanthone C and acremolin B produced by deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01.

2. Salvadenosine, a 5'-deoxy-5'-(methylthio) nucleoside from the Bahamian tunicate Didemnum sp.

Review 3. Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products.

4. Revision of the Structure of Acremine P from a Marine-Derived Strain of Acremonium persicinum.

5. Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems.