Glycocholic acid

Glycocholic acid
Glycocholic acid
Glycocholic acid
Names
IUPAC name
N-(3α,7α,12α-Trihydroxy-5β-cholan-24-oyl)glycine
Systematic IUPAC name
{(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.815 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1 checkY
    Key: RFDAIACWWDREDC-FRVQLJSFSA-N checkY
  • C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
C26H43NO6
Molar mass 465.631 g·mol−1
Melting point 130 °C (266 °F; 403 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate.

Metabolism

The enzyme choloylglycine hydrolase converts glycocholic acid, to cholic acid and glycine:

2D representation of the chemical structure of glycocholic acid.
glycocholic acid
 
H2O
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of cholic acid .
cholic acid
+
 
2D representation of the chemical structure of glycine.
glycine

In humans, the enzyme is an important component of the gut microbiome, where it metabolises many bile acids.

Clinical significance

In a prospective study, positive associations were observed between prediagnostic plasma levels of seven conjugated bile acid metabolites, including glycocholic acid, and colon cancer risk. These findings support experimental data suggesting that high circulating bile acids promote colon cancer risk.

See also

References

  1. ↑ "Glycocholic Acid". MeSH.
  2. ↑ Rossocha M, Schultz-Heienbrok R, von Moeller H, Coleman JP, Saenger W (2005). "Conjugated bile acid hydrolase is a tetrameric N-terminal thiol hydrolase with specific recognition of its cholyl but not of its tauryl product". Biochemistry. 44 (15): 5739–48. doi:10.1021/bi0473206. PMID 15823032.
  3. ↑ Marchesini, María Inés; Connolly, Joseph; Delpino, María Victoria; Baldi, Pablo C.; Mujer, Cesar V.; Delvecchio, Vito G.; Comerci, Diego J. (2011). "Brucella abortus Choloylglycine Hydrolase Affects Cell Envelope Composition and Host Cell Internalization". PLOS ONE. 6 (12) e28480. doi:10.1371/journal.pone.0028480. PMC 3234258. PMID 22174816.
  4. ↑ Bracken, Amy K.; Malarney, Kien P.; Chang, Pamela V. (2026). "Chemical Proteomics Reveals Regulation of Bile Salt Hydrolases via Oxidative Post-translational Modifications". Journal of the American Chemical Society. 148 (5): 5378–5386. doi:10.1021/jacs.5c18912. PMC 12903841. PMID 41612134.
  5. 1 2 Kühn T, Stepien M, López-Nogueroles M, Damms-Machado A, Sookthai D, Johnson T, Roca M, Hüsing A, Maldonado SG, Cross AJ, Murphy N, Freisling H, Rinaldi S, Scalbert A, Fedirko V, Severi G, Boutron-Ruault MC, Mancini FR, Sowah SA, Boeing H, Jakszyn P, Sánchez MJ, Merino S, Colorado-Yohar S, Barricarte A, Khaw KT, Schmidt JA, Perez-Cornago A, Trichopoulou A, Karakatsani A, Thriskos P, Palli D, Agnoli C, Tumino R, Sacerdote C, Panico S, Bueno-de-Mesquita B, van Gils CH, Heath AK, Gunter MJ, Riboli E, Lahoz A, Jenab M, Kaaks R (May 2020). "Prediagnostic Plasma Bile Acid Levels and Colon Cancer Risk: A Prospective Study". J Natl Cancer Inst. 112 (5): 516–524. doi:10.1093/jnci/djz166. PMC 7225675. PMID 31435679.
  6. ↑ Bernstein H, Bernstein C (January 2023). "Bile acids as carcinogens in the colon and at other sites in the gastrointestinal system". Exp Biol Med (Maywood). 248 (1): 79–89. doi:10.1177/15353702221131858. PMC 9989147. PMID 36408538.