메뉴 건너뛰기




Volumn 33, Issue 3, 1998, Pages 333-338

Rapid hydrolysis of bile acid conjugates using microwaves: Retention of absolute stereochemistry in the hydrolysis of (25R) 3α,7α,12α-trihydroxy- 5β-cholestan-26-oyltaurine

Author keywords

[No Author keywords available]

Indexed keywords

BILE ACID CONJUGATE; CHOLESTANOL; CHOLIC ACID DERIVATIVE; DIETHYLENE GLYCOL; LITHIUM SALT; PROPYLENE GLYCOL; SODIUM HYDROXIDE; TAUROCHOLIC ACID;

EID: 0031896692     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-998-0213-y     Document Type: Article
Times cited : (12)

References (41)
  • 1
    • 0026574020 scopus 로고
    • Peroxisome Assembly Mutations in Humans: Structural Heterogeneity in Zellweger Syndrome
    • Santos, M.J., Hoefler, S., Moser, A.B., Moser, H.W., and Lazarow, P.B. (1992) Peroxisome Assembly Mutations in Humans: Structural Heterogeneity in Zellweger Syndrome, J. Cell Physiol. 151, 103-112.
    • (1992) J. Cell Physiol. , vol.151 , pp. 103-112
    • Santos, M.J.1    Hoefler, S.2    Moser, A.B.3    Moser, H.W.4    Lazarow, P.B.5
  • 2
    • 0026523576 scopus 로고
    • A Human Gene Responsible for Zellweger Syndrome That Affects Peroxisome Assembly
    • Shimozawa, N., Tsukamoto, T., Suzuki, Y., Orii, T., Shirayshi, Y., Mori, T., and Fujiki, Y. (1992) A Human Gene Responsible for Zellweger Syndrome That Affects Peroxisome Assembly, Science 255, 1132-1134.
    • (1992) Science , vol.255 , pp. 1132-1134
    • Shimozawa, N.1    Tsukamoto, T.2    Suzuki, Y.3    Orii, T.4    Shirayshi, Y.5    Mori, T.6    Fujiki, Y.7
  • 3
    • 0026849933 scopus 로고
    • Mutations in the 70k Peroxisomal Membrane Protein Gene in Zellweger Syndrome
    • Gartner, J., Moser, H., and Valle, D. (1992) Mutations in the 70k Peroxisomal Membrane Protein Gene in Zellweger Syndrome, Nature Genet. 1, 16-23.
    • (1992) Nature Genet. , vol.1 , pp. 16-23
    • Gartner, J.1    Moser, H.2    Valle, D.3
  • 6
    • 0017573968 scopus 로고
    • The Enterohepatic Circulation of Bile Acids in Man
    • Hofmann, A.F. (1977) The Enterohepatic Circulation of Bile Acids in Man, Clin. Gastroenterol. 6, 3-24.
    • (1977) Clin. Gastroenterol. , vol.6 , pp. 3-24
    • Hofmann, A.F.1
  • 7
    • 0002348517 scopus 로고
    • The Enterohepatic Circulation
    • (Arias, I.M., Popper, H., Schachter, D., and Shafritz, D., eds.), Raven Press, New York
    • Carey, M.C. (1982) The Enterohepatic Circulation, in The Liver (Arias, I.M., Popper, H., Schachter, D., and Shafritz, D., eds.), pp. 429-465, Raven Press, New York.
    • (1982) The Liver , pp. 429-465
    • Carey, M.C.1
  • 10
    • 0004132923 scopus 로고
    • Methuen and Co. Ltd., London
    • Haslewood, G.A.D. (1967) Bile Salts, p. 16, Methuen and Co. Ltd., London.
    • (1967) Bile Salts , pp. 16
    • Haslewood, G.A.D.1
  • 11
    • 0014197616 scopus 로고
    • The Enzymatic Cleavage of the Carbon-Nitrogen Bond in 3α,7α,12α-Trihydroxy-5β-cholan-24-oylglycine
    • Nair, P.R., Gordon, M., and Rebach, J. (1967) The Enzymatic Cleavage of the Carbon-Nitrogen Bond in 3α,7α,12α-Trihydroxy-5β-cholan-24-oylglycine, J. Biol. Chem. 242, 7-11.
    • (1967) J. Biol. Chem. , vol.242 , pp. 7-11
    • Nair, P.R.1    Gordon, M.2    Rebach, J.3
  • 12
    • 0022466827 scopus 로고
    • Influence of the Amino Acid Moiety on Deconjugation of Bile Acid Amidates by Cholylglycine Hydrolase or Human Fecal Cultures
    • Huijghebaert, S.M., and Hofmann, A.F. (1986) Influence of the Amino Acid Moiety on Deconjugation of Bile Acid Amidates by Cholylglycine Hydrolase or Human Fecal Cultures, J. Lipid Res. 27, 742-752.
    • (1986) J. Lipid Res. , vol.27 , pp. 742-752
    • Huijghebaert, S.M.1    Hofmann, A.F.2
  • 13
    • 0021742094 scopus 로고
    • Substrate Specificity of Cholylglycine Hydrolase for the Hydrolysis of Bile Acid Conjugates
    • Batta, A.K., Salen, G., and Shefer, S. (1984) Substrate Specificity of Cholylglycine Hydrolase for the Hydrolysis of Bile Acid Conjugates, J. Biol. Chem. 259, 15035-15039.
    • (1984) J. Biol. Chem. , vol.259 , pp. 15035-15039
    • Batta, A.K.1    Salen, G.2    Shefer, S.3
  • 15
    • 26844530249 scopus 로고
    • Pancreatic Carboxypeptidase Hydrolysis of Bile Acid-Amino Acid Conjugates: Selective Resistance of Glycine and Taurine Amidates
    • abstract
    • Huijghebaert, S., and Hofmann, A.F. (1985) Pancreatic Carboxypeptidase Hydrolysis of Bile Acid-Amino Acid Conjugates: Selective Resistance of Glycine and Taurine Amidates, Gastroenterology 88, 1425 (abstract).
    • (1985) Gastroenterology , vol.88 , pp. 1425
    • Huijghebaert, S.1    Hofmann, A.F.2
  • 16
    • 0018581367 scopus 로고
    • Cleavage of the Taurine Conjugate of 3α,7α,12α-Trihydroxy-5β-cholestan-26-oic Acid by Rat Fecal Bacteria
    • Batta, A.K., Salen, G., Chang, F.W., and Shefer, S. (1979) Cleavage of the Taurine Conjugate of 3α,7α,12α-Trihydroxy-5β-cholestan-26-oic Acid by Rat Fecal Bacteria, J. Biol. Chem. 254, 11907-11909.
    • (1979) J. Biol. Chem. , vol.254 , pp. 11907-11909
    • Batta, A.K.1    Salen, G.2    Chang, F.W.3    Shefer, S.4
  • 18
    • 0025899968 scopus 로고
    • The Use of Microwave Oven for the Rapid Hydrolysis of Bile Acid Methyl Esters
    • Dayal, B., Salen, G., and Dayal, V. (1991) The Use of Microwave Oven for the Rapid Hydrolysis of Bile Acid Methyl Esters, Chem. Phys. Lipids 59, 97-103.
    • (1991) Chem. Phys. Lipids , vol.59 , pp. 97-103
    • Dayal, B.1    Salen, G.2    Dayal, V.3
  • 19
    • 0021612173 scopus 로고
    • Inability of Cholylglycine Hydrolase to Cleave the Amide Bond of Tauronorcholic Acid
    • Whitney, J.O., and Vessey, D.A. (1984) Inability of Cholylglycine Hydrolase to Cleave the Amide Bond of Tauronorcholic Acid, Steroids 44, 77-83.
    • (1984) Steroids , vol.44 , pp. 77-83
    • Whitney, J.O.1    Vessey, D.A.2
  • 20
    • 0021704117 scopus 로고
    • Synthesis, Intestinal Absorption and Metabolism of Sarcosine Conjugated Ursodeoxycholic Acid
    • Kimura, M., Hatono, S., Une, M., Fukuoka, C., Kuramoto, T., and Hoshita, T. (1984) Synthesis, Intestinal Absorption and Metabolism of Sarcosine Conjugated Ursodeoxycholic Acid, Steroids 43, 677-687.
    • (1984) Steroids , vol.43 , pp. 677-687
    • Kimura, M.1    Hatono, S.2    Une, M.3    Fukuoka, C.4    Kuramoto, T.5    Hoshita, T.6
  • 21
    • 0029043869 scopus 로고
    • Microwave-Induced Organic Reactions of Bile Acids: Esterification, Deformylation and Deacetylation Using Mild Reagents: Methane-sulfonic Acid/Methanol and or Para-Toluenesulfonic Acid/Methanol
    • Dayal, B., Rapole, K.R., and Salen, G. (1995) Microwave-Induced Organic Reactions of Bile Acids: Esterification, Deformylation and Deacetylation Using Mild Reagents: Methane-sulfonic Acid/Methanol and or Para-Toluenesulfonic Acid/Methanol, Steroids 60, 453-457.
    • (1995) Steroids , vol.60 , pp. 453-457
    • Dayal, B.1    Rapole, K.R.2    Salen, G.3
  • 22
  • 25
    • 0030991907 scopus 로고    scopus 로고
    • Rapid Hydrogenation of Unsaturated Sterols and Bile Alcohols Using Microwaves
    • Dayal, B., Ertel, N.H., Rapole, K.R., Asgaonkar, A., and Salen, G. (1997) Rapid Hydrogenation of Unsaturated Sterols and Bile Alcohols Using Microwaves, Steroids 62, 451-454.
    • (1997) Steroids , vol.62 , pp. 451-454
    • Dayal, B.1    Ertel, N.H.2    Rapole, K.R.3    Asgaonkar, A.4    Salen, G.5
  • 26
    • 0001358451 scopus 로고
    • Asymmetric Syntheses and Lanthanide-Induced CD Studies of (24R and 24S) 5β-Cholestane-3α,7α,12α,24,25-pentols
    • Dayal, B., Rao, Keshava, Seong, W.M., and Salen, G. (1994) Asymmetric Syntheses and Lanthanide-Induced CD Studies of (24R and 24S) 5β-Cholestane-3α,7α,12α,24,25-pentols, Pure Appl. Chem. 66, 2037-2040.
    • (1994) Pure Appl. Chem. , vol.66 , pp. 2037-2040
    • Dayal, B.1    Rao, K.2    Seong, W.M.3    Salen, G.4
  • 28
    • 0018538805 scopus 로고
    • X-Ray Diffraction Studies of 3α,7α,12α-Trihydroxy-5β-cholestan-26-oic Acid (THCA)
    • Batta, A.K., Salen, G., Blount, J.F., and Shefer, S. (1979) X-Ray Diffraction Studies of 3α,7α,12α-Trihydroxy-5β-cholestan-26-oic Acid (THCA), J. Lipid Res. 20, 935-940.
    • (1979) J. Lipid Res. , vol.20 , pp. 935-940
    • Batta, A.K.1    Salen, G.2    Blount, J.F.3    Shefer, S.4
  • 29
    • 0000442143 scopus 로고    scopus 로고
    • Environmentally Benign Chemistry: Microwave-Induced Stereocontrolled Synthesis of β-Lactam Synthons
    • Banik, B.K., Manhas, M.S., Robb, E.W., and Bose, A.K. (1997) Environmentally Benign Chemistry: Microwave-Induced Stereocontrolled Synthesis of β-Lactam Synthons, Heterocycles 44, 405-408.
    • (1997) Heterocycles , vol.44 , pp. 405-408
    • Banik, B.K.1    Manhas, M.S.2    Robb, E.W.3    Bose, A.K.4
  • 31
    • 0028891310 scopus 로고
    • Stereocontrol of β-Lactam Formation Using Microwave Irradiation
    • Bose, A.K., Banik, B.K., and Manhas, M.S. (1995) Stereocontrol of β-Lactam Formation Using Microwave Irradiation, Tetrahedon. Lett. 36, 213-216.
    • (1995) Tetrahedon. Lett. , vol.36 , pp. 213-216
    • Bose, A.K.1    Banik, B.K.2    Manhas, M.S.3
  • 33
    • 0029078472 scopus 로고
    • Microwave-Assisted Organic Reactions
    • Caddick, S. (1995) Microwave-Assisted Organic Reactions, Tetrahedon 51, 10403-10432.
    • (1995) Tetrahedon , vol.51 , pp. 10403-10432
    • Caddick, S.1
  • 34
    • 1842312507 scopus 로고
    • Applications of Microwave Energy in Organic Chemistry, A Review
    • Abramovitch, R.A. (1991) Applications of Microwave Energy in Organic Chemistry, A Review, Org. Prep. Proceed. Int. 23, 685-711.
    • (1991) Org. Prep. Proceed. Int. , vol.23 , pp. 685-711
    • Abramovitch, R.A.1
  • 35
    • 0030757788 scopus 로고    scopus 로고
    • Selective Oxidation of Sulfides to Sulfoxides and Sulfones by Microwave Thermolysis on Wet Silica-Supported Sodium Periodates
    • Verma, R.S., Saini, R.K., and Meshram, H.M. (1997) Selective Oxidation of Sulfides to Sulfoxides and Sulfones by Microwave Thermolysis on Wet Silica-Supported Sodium Periodates, Tetrahedron Lett. 37, 6525-6528.
    • (1997) Tetrahedron Lett. , vol.37 , pp. 6525-6528
    • Verma, R.S.1    Saini, R.K.2    Meshram, H.M.3
  • 36
    • 0027179608 scopus 로고
    • Base-Catalyzed Isomerization of Eugenol: Solvent-Free Conditions and Microwave Activation
    • Loupy, A., and Thach, N.C. (1993) Base-Catalyzed Isomerization of Eugenol: Solvent-Free Conditions and Microwave Activation, Synth. Commun. 23, 2571-2577.
    • (1993) Synth. Commun. , vol.23 , pp. 2571-2577
    • Loupy, A.1    Thach, N.C.2
  • 38
    • 33845279777 scopus 로고
    • Microwave-Induced Hydrolysis of Phosphoanhydride Bonds in Nucleotide Triphosphates
    • Sun, W.C., Guy, P.M., Jahngen, J.H., Rossomando, E.F., and Jahngen, E.G.E. (1988) Microwave-Induced Hydrolysis of Phosphoanhydride Bonds in Nucleotide Triphosphates, J. Org. Chem. 53, 4414-4416.
    • (1988) J. Org. Chem. , vol.53 , pp. 4414-4416
    • Sun, W.C.1    Guy, P.M.2    Jahngen, J.H.3    Rossomando, E.F.4    Jahngen, E.G.E.5
  • 39
    • 0024058679 scopus 로고
    • Purification and Characterization of Bile Salt Hydrolase from Clostridium perfringens
    • Gopal-Srivastava, R., and Hylemon, P.B. (1988) Purification and Characterization of Bile Salt Hydrolase from Clostridium perfringens, J. Lipid Res. 29, 1079-1085.
    • (1988) J. Lipid Res. , vol.29 , pp. 1079-1085
    • Gopal-Srivastava, R.1    Hylemon, P.B.2
  • 40
    • 0030570428 scopus 로고    scopus 로고
    • Substrate Stereospecificity in Oxidation of (25S)-3α,7α,12α-Trihydroxy-5β-cholestanoyl-CoA by Peroxisomal Trihydroxy-5β-cholestanoyl-CoA Oxidase
    • Bile Acids in Hepatobiliary Diseases: Basic Research and Clinical Application, (Paumgartner, G., Stiehl, A., and Gerok, W., eds.), Freiburg, Germany, October 22-24 (abstract 14)
    • Pedersen, J.I., Veggan, T., and Bjorkhem, I. (1996) Substrate Stereospecificity in Oxidation of (25S)-3α,7α,12α-Trihydroxy-5β-cholestanoyl-CoA by Peroxisomal Trihydroxy-5β-cholestanoyl-CoA Oxidase, in Bile Acids in Hepatobiliary Diseases: Basic Research and Clinical Application, Proceedings of the Falk in Symposium No. 93, XIV International Bile Acid Meeting, (Paumgartner, G., Stiehl, A., and Gerok, W., eds.), Freiburg, Germany, October 22-24 (abstract 14).
    • (1996) Proceedings of the Falk in Symposium No. 93, XIV International Bile Acid Meeting
    • Pedersen, J.I.1    Veggan, T.2    Bjorkhem, I.3
  • 41
    • 26844535530 scopus 로고    scopus 로고
    • Identification of a Unique Inborn Error in Bile Acid Conjugation Involving a Deficiency in Amidation
    • (Paumgartner, G., Stiehl, A., and Gerok, W., eds.), held in Freiburg, Germany, October 22-24 abstract
    • Setchell, K.D.R., Heubi, J.E., O'Connell, N.C., Hofmann A.F., and Lavine, J.E. (1996) Identification of a Unique Inborn Error in Bile Acid Conjugation Involving a Deficiency in Amidation, in Proceedings of the Falk Symposium. No. 93, XIV International Bile Acid Meeting, (Paumgartner, G., Stiehl, A., and Gerok, W., eds.), held in Freiburg, Germany, October 22-24 (abstract, pp. 9-10).
    • (1996) Proceedings of the Falk Symposium. No. 93, XIV International Bile Acid Meeting , pp. 9-10
    • Setchell, K.D.R.1    Heubi, J.E.2    O'Connell, N.C.3    Hofmann, A.F.4    Lavine, J.E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.