Acremolin from Acremonium strictum is N2,3-Etheno-2′-isopropyl-1-methylguanine, not a 1H-Azirine. Synthesis and Structural Revision

被引：27
作者：
Januar, Lawrence A. [1 ]
Molinski, Tadeusz F. [1 ,2 ]
机构：
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
[2] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 10期
关键词：
DNA-ADDUCTS; N2,3-ETHENOGUANOSINE; AZACYCLOPROPENE; 7-OXIDE;
D O I：
10.1021/ol400752s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 H-1-N-15-HMBC and fluorescence spectra.
引用
收藏
页码：2370 / 2373
页数：4
相关论文
共 33 条
  • [21] ENDOGENOUS DNA-ADDUCTS - POTENTIAL AND PARADOX
    MARNETT, LJ
    BURCHAM, PC
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 1993, 6 (06) : 771 - 785
  • [22] Exocyclic DNA Adducts as Biomarkers of Lipid Oxidation and Predictors of Disease. Challenges in Developing Sensitive and Specific Methods for Clinical Studies
    Medeiros, Marisa H. G.
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 2009, 22 (03) : 419 - 425
  • [23] DYSIDAZIRINE, A CYTO-TOXIC AZACYCLOPROPENE FROM THE MARINE SPONGE DYSIDEA-FRAGILIS
    MOLINSKI, TF
    IRELAND, CM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) : 2103 - 2105
  • [24] MONTGOMERY JA, 1962, J MED CHEM, V5, P15, DOI 10.1021/jm01236a002
  • [25] AZIRINES
    NAIR, V
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS-A SERIES OF MONOGRAPHS, 1983, 42 : 215 - 332
  • [26] SYNTHESIS OF GUANINE 7-OXIDE, AN ANTITUMOR ANTIBIOTIC FROM STREPTOMYCES SPECIES
    NOHARA, F
    NISHII, M
    OGAWA, K
    ISONO, K
    UBUKATA, M
    FUJII, T
    ITAYA, T
    SAITO, T
    [J]. TETRAHEDRON LETTERS, 1987, 28 (12) : 1287 - 1290
  • [27] OGAWA K, 1992, CHEM PHARM BULL, V40, P1315
  • [28] NEW AZACYCLOPROPENE DERIVATIVES FROM DYSIDEA-FRAGILIS COLLECTED IN POHNPEI
    SALOMON, CE
    WILLIAMS, DH
    FAULKNER, DJ
    [J]. JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (09): : 1463 - 1466
  • [29] 1,N2-ETHENOGUANINE AND N2,3-ETHENOGUANINE SYNTHESIS AND COMPARISON OF ELECTRONIC SPECTRAL PROPERTIES OF THESE LINEAR AND ANGULAR TRIHETEROCYCLES RELATED TO Y BASES
    SATTSANGI, PD
    LEONARD, NJ
    FRIHART, CR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (20) : 3292 - 3296
  • [30] Long-chain 2H-Azirines with heterogeneous terminal halogenation from the marine sponge Dysidea fragilis
    Skepper, Colin K.
    Molinski, Tadeusz F.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) : 2592 - 2597
1234