5-Pregnene-3β,20α-diol-3-sulfate-20- (2'-acetamido-2'-deoxy-α-D-glucoside) and 5-Pregnene-3β,20α-diol-3,20-disulfate. Two Novel Urinary Conjugates<sup>*</sup>

Arcos, Martha; Lieberman, Seymour

doi:10.1021/bi00859a022

Cited by 54 publications

(4 citation statements)

References 23 publications

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“…(5) the Cotton effect trough near 220 µ is often very intense, the residue rotation occasionally exceeding in magnitude that observed for the n-?r* band of the peptide bond in the a helix; analysis of helix content in glycoproteins containing significant quantities of -acetylglucosamine or its derivatives must therefore take into account these substantial rotations. Subsequent work in our laboratories (Lloyd et al, 1967(Lloyd et al, , 1968) and in those of others (Arcos and Lieberman, 1967) has confirmed the anticipated analytical utility of these measurements, especially when only milligram quantities of material are available. For example, the determination of structures of difucosyl and other oligosaccharides produced by alkaline degradation of blood group A, , H, and Lea substances was materially assisted by analysis of optical rotatory dispersion and circular dichroism spectra (Lloyd et al, 1967(Lloyd et al, , 1968.…”

mentioning

confidence: 55%

Optical activity and conformation of carbohydrates. II. Optical rotatory dispersion and circular dichroism studies on immunochemically reactive oligo- and polysaccharides containing amino sugars and their derivatives

Kabat¹,

Lloyd²,

Beychok³

1969

Biochemistry

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mentioning

confidence: 55%

Optical activity and conformation of carbohydrates. II. Optical rotatory dispersion and circular dichroism studies on immunochemically reactive oligo- and polysaccharides containing amino sugars and their derivatives

Kabat¹,

Lloyd²,

Beychok³

1969

Biochemistry

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“…Disaccharidic bilirubin conjugates containing hexuronic acid residues, aldobiuronic acid or pseudoaldobiuronic acid (Kuenzle, 1970c) have been demonstrated by means of their phenylazo derivatives. Mixed conjugates of steroids containing glucuronic acid and either glucopyranose (Williamson, Collins, Layne, Conrow & Bernstein, 1969; or N-acetylglucosamine (Layne, Sheth & Kirdani, 1964;Layne, 1965;Arcos & Lieberman, 1967;Collins, Williams & Layne, 1967;) have also been described. The glycosidic linkages of the steroid conjugates were shown to be in the :-D configuration (Collins et al 1967;Williamson et al 1969;Matsui & Fukushima, 1969).…”

Section: Discussionmentioning

confidence: 99%

Excretion in dog bile of glucose and xylose conjugates of bilirubin

Fevery

Hees

Leroy

et al. 1971

Biochemical Journal

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1. T.l.c. with neutral solvent systems of ethyl anthranilate azopigments derived from bile of man, dog and rat revealed pronounced species variation. The less polar components (alpha-group) could be separated conveniently by development with chloroform-methanol (17:3, v/v). 2. The azopigment material derived from gallbladder bile of dog contained about 10% of azobilirubin beta-d-monoxyloside (azopigment alpha(2)) and 30% of azobilirubin beta-d-monoglucoside (azopigment alpha(3)). The sugar moieties were identified by t.l.c. with acidic, neutral and basic solvent systems and by anion-exchange column chromatography of their boric acid complexes. Treatment of the purified azopigments with ammonia vapour led to the formation of the amide of azobilirubin, indicating that both pigments are ester glycosides. The beta-d configuration was demonstrated by enzymic studies with emulsin (an adequate source of beta-glucosidase activity) and with Mylase-P (an adequate source of beta-glucosidase and beta-xylosidase activities). 3. Hydrolysis studies with model substrates and with the alpha(2)- and alpha(3)-azopigments suggested that in Mylase-P the beta-glucosidase and beta-xylosidase activities reside in separate enzymes. 4. Compared with the accepted conjugation with glucuronic acid as a major route of detoxication in mammals, the detection of large amounts of xylose and glucose conjugates of bilirubin in dog bile suggests that the underlying biosynthetic pathways may be important alternative routes of detoxication.

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“…The GlcNAc moiety was attached to the 20α-hydroxy group, and the 3-hydroxy group was sulfated or glucuronidated. A GlcNAc conjugate of 5-pregnen-3α,20α-diol was first described by Arcos and Liebermann (134), but the physiological importance of this mode of conjugation of steroids and bile acids (see following discussion) remains unknown. However, it is of analytical interest since most methods will not include this type of conjugate in the analysis.…”

Section: Steroid Sulfates In Pregnancy and Intrahepatic Cholestasis Omentioning

confidence: 98%

Fifty years with bile acids and steroids in health and disease

Sjövall

2004

Lipids

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Cholesterol and its metabolites, e.g., steroid hormones and bile acids, constitute a class of compounds of great biological importance. Their chemistry, biochemistry, and regulation in the body have been intensely studied for more than two centuries. The author has studied aspects of the biochemistry and clinical chemistry of steroids and bile acids for more than 50 years, and this paper, which is an extended version of the Schroepfer Medal Award lecture, reviews and discusses part of this work. Development and application of analytical methods based on chromatography and mass spectrometry (MS) have been a central part of many projects, aiming at detailed characterization and quantification of metabolic profiles of steroids and bile acids under different conditions. In present terminology, much of the work may be termed steroidomics and cholanoidomics. Topics discussed are bile acids in human bile and feces, bile acid production, bacterial dehydroxylation of bile acids and steroids during the enterohepatic circulation, profiles of steroid sulfates in plasma of humans and other primates, development of neutral and ion-exchanging lipophilic derivatives of Sephadex for sample preparation and group separation of steroid and bile acid conjugates, profiles of steroids and bile acids in human urine under different conditions, hydroxylation of bile acids in liver disease, effects of alcohol-induced redox changes on steroid synthesis and metabolism, alcohol-induced changes of bile acid biosynthesis, compartmentation of bile acid synthesis studied with 3H-labeled ethanol, formation and metabolism of sulfated metabolites of progesterone in human pregnancy, abnormal patterns of these in patients with intrahepatic cholestasis of pregnancy corrected by ursodeoxycholic acid, inherited and acquired defects of bile acid biosynthesis and their treatment, conjugation of bile acids and steroids with N-acetylglucosamine, sulfate-glucuronide double conjugates of hydroxycholesterols, extrahepatic 7alpha-hydroxylation and 3-dehydrogenation of hydroxycholesterols, and extrahepatic formation of C27 bile acids. The final part discusses analysis of free and sulfated steroids in brain tissue by capillary liquid chromatography-electrospray MS and suggests a need for reevaluation of the function of steroid sulfates in rat brain.

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5-Pregnene-3β,20α-diol-3-sulfate-20- (2'-acetamido-2'-deoxy-α-D-glucoside) and 5-Pregnene-3β,20α-diol-3,20-disulfate. Two Novel Urinary Conjugates^*

Cited by 54 publications

References 23 publications

Optical activity and conformation of carbohydrates. II. Optical rotatory dispersion and circular dichroism studies on immunochemically reactive oligo- and polysaccharides containing amino sugars and their derivatives

Optical activity and conformation of carbohydrates. II. Optical rotatory dispersion and circular dichroism studies on immunochemically reactive oligo- and polysaccharides containing amino sugars and their derivatives

Excretion in dog bile of glucose and xylose conjugates of bilirubin

Fifty years with bile acids and steroids in health and disease

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5-Pregnene-3β,20α-diol-3-sulfate-20- (2'-acetamido-2'-deoxy-α-D-glucoside) and 5-Pregnene-3β,20α-diol-3,20-disulfate. Two Novel Urinary Conjugates*

Cited by 54 publications

References 23 publications

Optical activity and conformation of carbohydrates. II. Optical rotatory dispersion and circular dichroism studies on immunochemically reactive oligo- and polysaccharides containing amino sugars and their derivatives

Optical activity and conformation of carbohydrates. II. Optical rotatory dispersion and circular dichroism studies on immunochemically reactive oligo- and polysaccharides containing amino sugars and their derivatives

Excretion in dog bile of glucose and xylose conjugates of bilirubin

Fifty years with bile acids and steroids in health and disease

Contact Info

Product

Resources

About

5-Pregnene-3β,20α-diol-3-sulfate-20- (2'-acetamido-2'-deoxy-α-D-glucoside) and 5-Pregnene-3β,20α-diol-3,20-disulfate. Two Novel Urinary Conjugates^*