Pikromycin

Pikromycin
Names
IUPAC name
(3R,5R,6S,7S,9R,11E,13S,14R)-14-Ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-6-[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyloxy]-1-oxacyclotetradec-11-ene-2,4,10-trione
Systematic IUPAC name
(3R,5R,6S,7S,9R,11E,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione
Other names
Picromycin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C28H47NO8/c1-10-22-28(7,34)12-11-21(30)15(2)13-16(3)25(18(5)23(31)19(6)26(33)36-22)37-27-24(32)20(29(8)9)14-17(4)35-27/h11-12,15-20,22,24-25,27,32,34H,10,13-14H2,1-9H3/b12-11+/t15-,16+,17-,18+,19-,20+,22-,24-,25+,27+,28+/m1/s1 checkY
    Key: UZQBOFAUUTZOQE-VSLWXVDYSA-N checkY
  • InChI=1S/C28H47NO8/c1-10-22-28(7,34)12-11-21(30)15(2)13-16(3)25(18(5)23(31)19(6)26(33)36-22)37-27-24(32)20(29(8)9)14-17(4)35-27/h11-12,15-20,22,24-25,27,32,34H,10,13-14H2,1-9H3/b12-11+/t15-,16+,17-,18+,19-,20+,22-,24-,25+,27+,28+/m1/s1
  • O=C2[C@@H]([C@@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@@H](C)C[C@H](C(=O)/C=C/[C@@](O)(C)[C@H](OC(=O)[C@@H]2C)CC)C)C
Properties
C28H47NO8
Molar mass 525.683 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pikromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated.[1] Pikromycin is synthesized through a type I polyketide synthase system in Streptomyces venezuelae, a species of Gram-positive bacterium in the genus Streptomyces.[2] Pikromycin is derived from narbonolide, a 14-membered ring macrolide. [3] Along with the narbonolide backbone, pikromycin includes a desosamine sugar and a hydroxyl group. Although Pikromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as ertythromycins and new epothilones. [4]

  1. ^ Brockmann, H. & Henkel, W. (1951). "Pikromycin, ein bitter schmeckendes Antibioticum aus Actinomyceten". Ntibiotica aus Actinomyceten. 84: 184–288. doi:10.1002/cber.19510840306.
  2. ^ Y. Xue & D. Sherman (2001). "Biosynthesis and Combinatorial Biosynthesis of Pikromycin-Related Macrolides in Streptomyces venezuelae". Metabolic Engineering. 3 (1): 15–26. doi:10.1006/mben.2000.0167. PMID 11162229.
  3. ^ Maezawa, T. Hori, A. Kinumaki and M. Suzuki (1973). "Biological conversion of narbonolide to picromycin". The Journal of Antibiotics. 26 (12): 771–775. doi:10.7164/antibiotics.26.771. PMID 4792390.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ J.D. Kittendorf & D.H. Sherman (2009). "The Methymycin/Pikromycin Biosynthetic Pathway: A Model for Metabolic Diversity in Natural Product". Bioorg Med Chem. 17 (6): 2137–2146. doi:10.1016/j.bmc.2008.10.082. PMC 2843759. PMID 19027305.