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Yuremamine

From Wikipedia, the free encyclopedia
Yuremamine
Names
Other names
Yuremamine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C27H28N2O6/c1-29(2)10-9-17-16-5-3-4-6-19(16)28-24(17)23-18-8-7-15(30)13-22(18)35-27(26(23)34)14-11-20(31)25(33)21(32)12-14/h3-8,11-13,23,26-28,30-34H,9-10H2,1-2H3/t23-,26+,27-/m0/s1
    Key: KXDXQDYTLNRCHP-RNJDCESWSA-N
  • CN(C)CCC1=C(NC2=CC=CC=C12)[C@@H]1[C@H](O)[C@H](OC2=C1C=CC(O)=C2)C1=CC=CC=C1
Properties
C27H28N2O6
Molar mass476.529 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Yuremamine is aphytoindolealkaloid which was isolated from the bark ofMimosa tenuiflora in 2005, and erroneously assigned a pyrrolo[1,2-a]indole structure that was thought to represent a new class ofindole alkaloids.[2] However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be aflavonoid derivative.[3] It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, but total synthesis revealed that yuremamine as afree base is colorless, and the formation of atrifluoroacetate salt duringHPLC purification is what led to the purple appearance.[3]

Originally proposed chemical structure of yuremamine

References

[edit]
  1. ^Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (26 January 2010).Dictionary of Alkaloids with CD-ROM. CRC Press. p. 2033.ISBN 978-1-4200-7770-4.
  2. ^Vepsäläinen, J. J.; Auriola, S.; Tukiainen, M.; Ropponen, N. & Callaway, J. (2005). "Isolation and characterization of Yuremamine, a new phytoindole".Planta Medica.71 (11):1049–1053.doi:10.1055/s-2005-873131.PMID 16320208.S2CID 260250347.
  3. ^abCalvert, Matthew B.; Sperry, Jonathan (2015). "Bioinspired total synthesis and structural revision of yuremamine, an alkaloid from the entheogenic plant Mimosa tenuiflora".Chemical Communications.51 (28):6202–6205.doi:10.1039/c5cc00380f.PMID 25756921.
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