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Calyculin

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Calyculins

Calyculins A and C
Names
IUPAC name ((2R,3R,5R,7R,8S,9S)-2-((1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl)-9-((E)-3-(2-((2S)-4-(((2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanoyl)amino)butan-2-yl)-1,3-oxazol-4-yl)prop-2-enyl)-7-hydroxy-4,4,8-trimethyl-1,10-dioxaspiro(4.5)decan-3-yl) dihydrogen phosphate (Calyculin A)
Identifiers
CAS Number
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m1/s1Key: FKAWLXNLHHIHLA-LIKMAGLISA-N
Properties
Chemical formula C51H83N4O15P (Calyculin C)
Molar mass 1023.2 g/mol (Calyculin C)
Properties
Chemical formula C50H81N4O15P (Calyculin A)
Molar mass 1009.17 g/mol (Calyculin A)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Calyculins are natural products originally isolated from the marine sponge Discodermia calyx. Calyculins have proven to be strong serine/threonine protein phosphatase inhibitors and based on this property, calyculins might be potential tumor-promoting agents.

A laboratory synthesis of calyculin A has been reported.

Biosynthesis

Calyculin A is biosynthesized as a pyrophosphate containing phosphocalyculin A protoxins by a hybrid PKS-NRPS pathway within the sponge bacterial symbiont, "Candidatus Entotheonella" sp.

References

  1. "Calyculin A" (PDF). Cell Signaling Technology. 2015-01-02.
  2. Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T (1990). "Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin". Cancer Res. 50 (12): 3521–3525. PMID 2160320.
  3. Tanimoto, Norihiko; Gerritz, Samuel W.; Sawabe, Akiyoshi; Noda, Takeshi; Filla, Sandra A.; Masamune, Satoru (1994-03-17). "Synthese von natürlich vorkommendem (−)‐Calyculin A". Angewandte Chemie. 106 (6): 674–677. doi:10.1002/ange.19941060611. ISSN 0044-8249.
  4. Jomori, Takahiro; Matsuda, Kenichi; Egami, Yoko; Abe, Ikuro; Takai, Akira; Wakimoto, Toshiyuki (2021). "Insights into phosphatase-activated chemical defense in a marine sponge holobiont". RSC Chemical Biology. 2 (6): 1600–1607. doi:10.1039/D1CB00163A. ISSN 2633-0679. PMC 8637855. PMID 34977575.
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