Characterization of Non-enzymatic Acylation of Amino or Thiol Groups of Bionucleophiles by the Acyl-adenylate or Acyl-CoA Thioester of Cholic Acid

Analytical and Bioanalytical Chemistry

Volumn 400, Issue 7, 2011, Pages 2253-2259

  Mitamura, Kuniko ^a   Aoyama, Eriko ^a   Sakai, Toshihiro ^a   Iida, Takashi ^b   Hofmann, Alan F ^c   Ikegawa, Shigeo ^a  

^a KINKI UNIVERSITY   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

Glutathione; Glycine; Liquid chromatography electrospray ionization mass spectrometry; N acetylcysteine; Taurine

Indexed keywords

ACCEPTOR MOLECULES; ACYL-COA; AMINO GROUP; BILE ACID; CARBONYL CARBON; CHOLIC ACIDS; DETECTION MODE; ELECTROPHILICITY; GLUTATHIONES; GLYCINE; ION-TRAP MASS SPECTROMETRY; ISOTOPICALLY LABELED; N-ACETYLCYSTEINE; NON-ENZYMATIC; NUCLEOPHILIC GROUPS; NUCLEOPHILICITIES; TAURINE; THIOESTERS; THIOL GROUPS;

ACYLATION; CHROMATOGRAPHY; ELECTROSPRAY IONIZATION; IONIZATION; LIQUIDS; MASS SPECTROMETRY; METABOLISM; METABOLITES; PROTEINS;

AMINO ACIDS;

ADENOSINE PHOSPHATE; CHOLIC ACID; COENZYME A; ESTER;

ACYLATION; ARTICLE; CHEMISTRY;

ACYLATION; ADENOSINE MONOPHOSPHATE; CHOLIC ACID; COENZYME A; ESTERS;

EID: 79956269497     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-011-4961-z     Document Type: Article

References (20)

1. MA Polokoff RA Coleman RM Bell 1979 Evidence that cholic acid CoA ligase is located asymmetrically on the cytoplasmic surface of hepatic microsomal vesicles J Lipid Res 20 17 21 1:CAS:528:DyaE1MXhtlCmsbo%3D
2. WC Lim TW Jordan 1981 Subcellular distribution of hepatic bile acid-conjugating enzymes Biochem J 197 611 618 1:CAS:528:DyaL38Xjt1WjtQ%3D%3D (Pubitemid 11031125)
3. FA Simion B Fleischer S Fleischer 1983 Subcellular distribution of cholic acid:coenzyme A ligase and deoxycholic acid:coenzyme A ligase activities in rat liver Biochemistry 22 5029 5034 10.1021/bi00290a023 1:CAS:528: DyaL3sXltlOhsL4%3D
4. BF Kase K Prydz I Björkhem JI Pedersen 1986 In vitro formation of bile acids from di- and trihydroxy-5β-cholestanoic acid in human liver peroxisomes Biochim Biophys Acta 877 37 42 1:CAS:528:DyaL28XktlOlsrw%3D (Pubitemid 16060190)
5. DA Vessey AM Benfatto ES Kempner 1987 Bile acid:CoASH ligases from guinea pig and porcine liver microsomes. Purification and characterization J Biol Chem 262 5360 5365 1:CAS:528:DyaL2sXhvFWlt7s%3D
6. BF Kase I Björkhem 1989 Peroxisomal bile acid-CoA:amino-acid N-acyltransferase in rat liver J Biol Chem 264 9220 9223 1:CAS:528: DyaL1MXktlKqt7s%3D (Pubitemid 19157556)
7. SJ Steinberg SJ Mihalik DG Kim DA Cuebas PA Watkins 2000 The human liver-specific homolog of very long-chain acyl-CoA synthetase is cholate:CoA ligase J Biol Chem 275 15605 15608 10.1074/jbc.C000015200 1:CAS:528: DC%2BD3cXjvFajuro%3D (Pubitemid 30366853)
8. M Kelly DA Vessey 1994 Determination of the mechanism of reaction for bile acid:CoA ligase Biochem J 304 945 949
9. S Ikegawa H Ishikawa H Oiwa M Nagata J Goto T Kozaki M Gotowda N Asakawa 1999 Characterization of cholyl-adenylate in rat liver microsomes by liquid chromatography/electrospray ionization-mass spectrometry Anal Biochem 266 125 132 10.1006/abio.1998.2944 1:CAS:528:DyaK1MXisV2ktQ%3D%3D (Pubitemid 29024616)
10. N Mano M Uchida H Okuyama I Sasaki S Ikegawa J Goto 2001 Simultaneous detection of cholyl adenylate and coenzyme A thioester utilizing liquid chromatography/electrospray ionization mass spectrometry Anal Sci 17 1037 1042 10.2116/analsci.17.1037 1:CAS:528:DC%2BD3MXntFWqtbs%3D (Pubitemid 32963532)
11. J Goto M Nagata N Mano N Kobayashi S Ikegawa R Kiyonami 2001 Bile acid acyl adenylate: a possible intermediate to produce a protein-bound bile acid Rapid Commun Mass Spectrom 15 104 109 10.1002/1097-0231(20010130)15:2<104:: AID-RCM198>3.0.CO;2-N 1:CAS:528:DC%2BD3MXns1emuw%3D%3D (Pubitemid 32066739)
12. N Mano K Kasuga N Kobayashi J Goto 2004 A nonenzymatic modification of the amino-terminal domain of histone H3 by bile acid acyl adenylate J Biol Chem 279 55034 55041 10.1074/jbc.M409205200 1:CAS:528:DC%2BD2cXhtFeis77P (Pubitemid 40066495)
13. K Mitamura M Sogabe H Sakanashi S Watanabe T Sakai Y Yamaguchi T Wakamiya S Ikegawa 2007 Analysis of bile acid glutathione thioesters by liquid chromatography/electrospray ionization-tandem mass spectrometry J Chromatogr B 855 88 97 10.1016/j.jchromb.2007.02.010 1:CAS:528:DC%2BD2sXotVGmsL8%3D (Pubitemid 47077723)
14. K Mitamura S Watanabe T Sakai R Okihara M Sogabe T Wakamiya AF Hofmann S Ikegawa 2009 Chemical synthesis of N-acetylcysteine conjugates of bile acids and in vivo formation in cholestatic rats as shown by liquid chromatography/ electrospray ionization-linear ion trap mass spectrometry J Chromatogr B 877 2630 2638 10.1016/j.jchromb.2009.03.029 1:CAS:528:DC%2BD1MXpt1Kis7o%3D
15. K Mitamura S Watanabe Y Mitsumoto T Sakai M Sogabe T Wakamiya S Ikegawa 2009 Formation and biliary excretion of glutathione conjugates of bile acids in the rat as shown by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry Anal Biochem 384 224 230 10.1016/j.ab.2008.09.040 1:CAS:528:DC%2BD1cXhsVGgs77P
16. K Mitamura N Hori T Iida AF Hofmann S Ikegawa 2011 Identification of bile acid S-acyl glutathione conjugates in rat bile by liquid chromatography/ electrospray ionization-linear ion trap mass spectrometry Steroids 76 68 77 10.1016/j.steroids.2010.09.002 1:CAS:528:DC%2BC3cXhsF2gtb%2FE
17. S Ikegawa H Ito M Ohshima M Maeda AF Hofmann 2009 Chemical synthesis of bile acid acyl-adenylates and formation by a rat liver microsomal fraction Steroids 74 751 757 10.1016/j.steroids.2009.04.003 1:CAS:528: DC%2BD1MXnsFOktr0%3D
18. PP Nair G Kessie R Patnaik C Guidry 1994 Isolation and HPLC of N-ε-lithocholyl lysine as its fluorescamine and dimethylaminoazobenzene isothiocyanate derivatives Steroids 59 212 216 10.1016/0039-128X(94)90030-2 1:CAS:528:DyaK2cXmtVGqs7g%3D (Pubitemid 24083727)
19. S Ikegawa T Yamamoto H Ito S Ishiwata T Sakai K Mitamura M Maeda 2008 Immunoprecipitation and MALDI-MS identification of lithocholic acid-tagged proteins in liver of bile duct-ligated rats J Lipid Res 49 2463 2473 10.1194/jlr.M800350-JLR200 1:CAS:528:DC%2BD1cXht12it7jN
20. S Ikegawa N Murao M Nagata S Ohba J Goto 1999 Covalent binding of bile acid acyl glucuronide with protein Anal Sci 15 213 215 10.2116/analsci.15.213 1:CAS:528:DyaK1MXhvVOgtL4%3D