Taurodeoxycholic acid

Taurodeoxycholic acid is a bile acid. This compound is a closely related isomer of Taurochenodeoxycholic acid and Tauroursodeoxycholic acid sharing the exact molecular formula and molecular weight.

Taurodeoxycholic acid
Names
IUPAC name
2-(3α,12α-Dihydroxy-5β-cholan-24-amido)ethane-1-sulfonic acid
Systematic IUPAC name
2-{(2R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11S,11aR)-7,11-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}ethane-1-sulfonic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1 checkY
    Key: AWDRATDZQPNJFN-VAYUFCLWSA-N checkY
  • InChI=1/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
    Key: AWDRATDZQPNJFN-VAYUFCLWBR
  • C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Properties
C26H45NO6S
Molar mass 499.71 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Mass Spectrometry Interference with PFOS

Benskin and colleagues (https://pubs.acs.org/doi/pdf/10.1021/ac070802d) published in 2007 an article identifying Taurodeoxycholic acid and isomers as mass spectrometry interferents with PFOS (Perfluorooctanesulfonic acid) as the two compounds share the m/z transition of 498-80. The molecular weight of PFOS and taurodeoxycholic acid and isomers are similar enough in molecular weight that most low resolution Triple quadrupole mass spectrometer are unable to distinguish these two chemicals from each other. Additionally both compounds share a Sulfonate group (leading to the m/z 80 loss) in the common mass spectrometry transition. Reiner and colleagues https://pubs.acs.org/doi/pdf/10.1021/es800770f found these bile acid compounds in chicken eggs and suggest that monitoring for m/z 99 (FSO3 loss) as does Benskin and colleagues noted above.

Compounding the issue is PFOS is widely distributed in global wildlife, and analysis of blood, liver and flesh of monitored wildlife will likely also contain these bile acids. Therefore caution must be taken in sample cleanup, analysis and mass spectra interpretations. Strynar and colleagues ASMS Strynar et al., 2009 demonstrated the presence of these cholic acids in a number of biological samples. Additionally they gave suggestions for removal of this interferent issue during PFOS analysis including the use of high resolution mass spectrometry (Time-of-flight mass spectrometry) that is able to resolve PFOS (monoisotopic mass 498.9302) from cholic acids (monoisotopic mass 498.2895) easily. Additional suggestions included removal of cholic acids through the Solid-phase extraction cleanup of methanolic extracts using Supelco's ENVI-Carb cartridge or monitoring for the presence of cholic acids via m/z 498-124 and 498-107 which PFOS does not respond to.

References
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