Kendomycin

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Kendomycin[1]
Names
IUPAC name
(1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.16,9.02,7]tetracosa-2,5,7,14-tetraen-4-one
Systematic IUPAC name
(1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.16,9.02,7]tetracosa-2,5,7,14-tetraen-4-one
Other names
(-)-TAN 2162
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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MeSH C485395
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  • InChI=1S/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1 ☒N
    Key: HKLDUJXJTQJSEJ-OLXNOMCWSA-N ☒N
  • InChI=1/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1
    Key: HKLDUJXJTQJSEJ-OLXNOMCWBE
  • C[C@H]\1CC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C3=C(C(=O)C(=C4C3=C[C@@](O4)([C@H](C[C@@H](C/C(=C1)/C)C)C)O)C)O)C)O)C
Properties
C29H42O6
Molar mass 486.64 g/mol
Appearance Yellow powder
Solubility in DMSO, methanol Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Kendomycin is an anticancer macrolide first isolated from Streptomyces violaceoruber.[2] It has potent activity as an endothelin receptor antagonist and anti-osteoporosis agent.[3] It also has strong cytotoxicity against various tumor cell lines.[2]

Total synthesis

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Because of its potent biological activities, kendomycin has attracted interest as a target of total synthesis. The first total synthesis of kendomycin was accomplished by Lee and Yuan in 2004.[4] The total number of syntheses stands at 6.[5][6][7][8][9]

References

[edit | edit source]
  1. ^ Kendomycin Archived 2008-05-16 at the Wayback Machine at Alexis-Biochemicals
  2. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Burke Research Group Archived 2006-08-29 at the Wayback Machine University of Wisconsin
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