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Ergocryptine

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alpha-Ergocryptine
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.384 Edit this at Wikidata
Chemical and physical data
FormulaC32H41N5O5
Molar mass575.698 g/mol g·mol−1
3D model (JSmol)
  • O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3CC(C)C)(NC(=O)[C@@H]7/C=C6/c4cccc5c4c(cn5)C[C@H]6N(C)C7)C(C)C
  • InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1 ☒N
  • Key:YDOTUXAWKBPQJW-NSLWYYNWSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Ergocryptine is an ergopeptine and one of the ergot alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine.[1]

Chemistry

Ergocryptine is a mixture of two very similar compounds, alpha- and beta-ergocryptine.[2] The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine.

See also

References

  1. ^ Kren V., Cvak L. "Ergot: the genus Claviceps". Amsterdam: Harwood Academic Publishers; 1999. p. 399–401
  2. ^ Yates, S. G.; Plattner, R. D.; Garner, G. B. (1985). "Detection of ergopeptine alkaloids in endophyte-infected, toxic Ky-31 tall fescue by mass spectrometry/mass spectrometry" (PDF). Journal of Agricultural and Food Chemistry. 33 (4): 719. doi:10.1021/jf00064a038.


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