Spicamycin

Spicamycin is an antibiotic with the molecular formula C30H51N7O7 which is produced by the bacterium Streptomyces alanosinicus.[1][2][3] Spicamycin also shows antitumor activity.[3]

Spicamycin
Names
IUPAC name
N-[2-[[2-(1,2-dihydroxyethyl)-4,5-dihydroxy-6-(7H-purin-6-ylamino)oxan-3-yl]amino]-2-oxoethyl]-14-methylpentadecanamide
Other names
Septacidin, NSC65104
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C30H51N7O7/c1-19(2)13-11-9-7-5-3-4-6-8-10-12-14-21(40)31-15-22(41)36-23-25(42)26(43)30(44-27(23)20(39)16-38)37-29-24-28(33-17-32-24)34-18-35-29/h17-20,23,25-27,30,38-39,42-43H,3-16H2,1-2H3,(H,31,40)(H,36,41)(H2,32,33,34,35,37)
    Key: YBZRLMLGUBIIDN-UHFFFAOYSA-N
  • N(C1=C2C(N=CN2)=NC=N1)[C@H]3O[C@@]([C@H](CO)O)([C@H](NC(CNC(CCCCCCCCCCCCC(C)C)=O)=O)[C@@H](O)[C@H]3O)[H]
Properties
C30H51N7O7
Molar mass 621.780 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

References
  1. Burger, AM; Kaur, G; Hollingshead, M; Fischer, RT; Nagashima, K; Malspeis, L; Duncan, KL; Sausville, EA (March 1997). "Antiproliferative activity in vitro and in vivo of the spicamycin analogue KRN5500 with altered glycoprotein expression in vitro". Clinical Cancer Research. 3 (3): 455–63. PMID 9815705.
  2. "Septacidin". Pubchem.ncbi.NLM.nih.gov.
  3. Omura, Satoshi (6 December 2012). The Search for Bioactive Compounds from Microorganisms. Springer Science & Business Media. p. 107. ISBN 978-1-4612-4412-7.

Further reading
  • Suzuki, Tamotsu; Suzuki, Sayaka T.; Yamada, Iwao; Koashi, Yoshiaki; Yamada, Kazue; Chida, Noritaka (1 May 2002). "Total Synthesis of Spicamycin". The Journal of Organic Chemistry. 67 (9): 2874–2880. doi:10.1021/jo010925c. PMID 11975540.
  • Suzuki, Tamotsu; Chida, Noritaka (February 2003). "The New and Efficient Synthesis of a Heptose Moiety of Spicamycin". Chemistry Letters. 32 (2): 190–191. doi:10.1246/cl.2003.190.


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