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Altemicidin

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Altemicidin
Names
IUPAC name (4aR,6S,7R,7aS)-4-carbamoyl-6-hydroxy-2-methyl-7-(2-sulfamoylacetamido)-2,4a,5,6,7,7a-hexahydro-1H-cyclopentapyridine-7-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1Key: VZRFZUPFQKSXPV-VPFIQFBESA-N
  • InChI=1/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1Key: VZRFZUPFQKSXPV-VPFIQFBEBF
SMILES
  • O=S(=O)(N)CC(=O)N2(C(=O)O)(O)C1C(=C/N(C12)C)\C(=O)N
Properties
Chemical formula C13H20N4O7S
Molar mass 376.39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Altemicidin is monoterpene alkaloid first identified in isolates from marine actinomycetes (specifically Streptomyces sioyaensis) in 1989. It may also be produced synthetically. Altemicidin displays both acaricidal and antitumor activity.

References

  1. ^ Takahashi, Atsushi; Kurasawa, Shogo; Ikeda, Daishiro; Okami, Yoshiro; Takeuchi, Tomio (1989). "Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties". The Journal of Antibiotics. 42 (11): 1556–1561. doi:10.7164/antibiotics.42.1556. ISSN 0021-8820. PMID 2584137.
  2. Takahashi, Atsushi; Ikeda, Daishiro; Nakamura, Hikaru; Naganawa, Hiroshi; Kurasawa, Shogo; Okami, Yoshiro; Takeuchi, Tomio; Iitaka, Yoichi (1989). "Altemicidin, a new acaricidal and antitumor substance. II. Structure determination". The Journal of Antibiotics. 42 (11): 1562–1566. doi:10.7164/antibiotics.42.1562. ISSN 0021-8820. PMID 2584138.
  3. Kende, Andrew S.; Liu, Kun; Jos Brands, K. M. (1995). "Total Synthesis of (-)-Altemicidin: A Novel Exploitation of the Potier-Polonovski Rearrangement". Journal of the American Chemical Society. 117 (42): 10597–10598. doi:10.1021/ja00147a032. ISSN 0002-7863.
  4. Kan, Toshiyuki; Kawamoto, Yuichiro; Asakawa, Tomohiro; Furuta, Takumi; Fukuyama, Tohru (2008). "Synthetic Studies on Altemicidin: Stereocontrolled Construction of the Core Framework". Organic Letters. 10 (2): 169–171. doi:10.1021/ol701940f. ISSN 1523-7060. PMID 18081299.


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