Naphthomycin A

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Naphthomycin A
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
  • InChI=1S/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9-,16-14-,21-13-,23-12-,25-17-/t20-,22-,24-,27-,29-,35-/m0/s1
    Key: AXEGRHYJHHPVDH-GGBROUGNSA-N
  • O=C1c2c3C(=O)/C(=C1/Cl)NC(=O)/C(=C\C=C\C=C/[C@H](C)[C@@H](O)CC(=O)\C(=C/C[C@H](O)\C=C/[C@H](C)[C@H](O)[C@H](\C=C(\C(=O)c2c(O)c(c3)C)C)C)C)C
Properties
C40H46ClNO9
Molar mass 720.26 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Naphthomycin A is a type of naphthomycin. It was isolated as a yellow pigment from Streptomyces collinus and it shows antibacterial, antifungal, and antitumor activities.[1] Naphthomycins have the longest ansa aliphatic carbon chain of the ansamycin family.[2] Biosynthetic origins of the carbon skeleton from PKS1 were investigated by feeding 13C-labeled precursors and subsequent 13C-NMR product analysis. Naphthomycin gene clusters have been cloned and sequenced to confirm involvement in biosynthesis via deletion of a 7.2kb region.[3] Thirty-two genes were identified in the 106kb cluster.[4]

The proposed naphthomycin biosynthetic pathway.[5] A, adenylation; KS, ketosynthase; AT, acyltransferase; T, acyl carrier protein or peptidyl carrier protein; DH, dehydratase; KR, ketoreductase; (*) redundant domain.

References

  1. PMID 22193711
    .
  2. S2CID 31145406
    .
  3. ^ Bai, L.; Y. Wu; Q. Kang; Y. Shen; Z. Deng (2012). Patent. CN: 2012-10300294: 225. {{cite journal}}: Missing or empty |title= (help)
  4. PMID 9512878
    .
  5. PMID 22193711
    .
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