
CAS Name: b-D-Glucopyranose 1-(3,4,5-trihydroxybenzoate)
Additional Names: b-D-glucopyranose-1-gallate; glucogallic acid; 1-galloyl-b-D-glucose
Percent Composition: C 46.99%, H 4.85%, O 48.1...
Literature References: Glucoside or glucotannoid from chinese rhubarb, Rheum officinale, Baill., Polygonaceae: Gilson, Compt. Rend. 136, 385 (1903). Structure and synthesis: Fischer, Bergmann, Ber. 51, 1760 (1918); Schmidt, Schmadel, Ann. 649, 149 (1961).
Trademarks: Glusulase (Endo)
Literature References: Glucuronide-splitting enzyme found in liver, spleen, and certain tissues of the endocrine and reproductive systems. Rats seem to have a higher concn than other mammals. Also found in fish liver, snails, mollusks, and some insects. Isoln from rat livers, kidneys, and spleens: Fishman, Talalay, Science 105, 131 (1947). Review and bibliography: Fishman, Adv. Enzymol. 16, 361-409 (1955).
CAS Name: 3-Pyridinecarboxylic acid 2-[2-(4-chlorophenoxy)-2-methyl-1-oxopropoxy]ethyl ester
Additional Names: nicotinic acid 2-hydroxyethyl ester 2-(p-chlorophenoxy)-2-methylpropionate (ester)...
Literature References: Glycol diester of nicotinic and clofibric acids, q.q.v. Prepn: A. Scherm, D. Peteri, DE 1941217; eidem, US 3723446 (1971, 1973 both to Merz). Lipid lowering effects in rats: W. Sterner, A. Schultz, Arzneim.-Forsch. 24, 1990 (1974). Metabolism: H. Oelschläger et al., ibid. 30, 984 (1980). In vitro effect on human platelet function: M. P. Ortega et al., Thromb. Res. 19, 409 (1980). HPLC determn in plasma: E. R. Garrett, M. R. Gardner, J. Pharm. Sci. 71, 14 (1982). Bioavailability and pharmacokinetics in humans: K. I. Johnson et al., Arzneim.-Forsch. 34, 1785 (1984). Review of pharmacology and comparison with other hypolipidemic agents: R. Paoletti et al., Am. J. Cardiol. 52, Suppl B, 21B-27B (1983).
CAS Name: Methyl-a-D-glucopyranoside 6-(heptylcarbamate)
Additional Names: 6-O-(N-heptylcarbamoyl)-methyl-a-D-glucopyranoside
Percent Composition: C 53.72%, H 8.72%, N 4.18%, O 33.39%
Literature References: Glycolipid surfactant. Prepn: D. Plusquellec et al., Anal. Biochem. 179, 145 (1989). Kinetics of surfactant exchange; effect on micelle aggregation: M. Frindi et al., J. Phys. Chem. 96, 8137 (1992). Crystal structure: S. B. Engelsen et al., Carbohydr. Res. 264, 161 (1994). Assessment as detergent in biochemical applications: M. B. Ruiz et al., Biochim. Biophys. Acta 1193, 301 (1994). Use in protein purification: M. C. Sanders et al., J. Biol. Chem. 271, 2651 (1996); P. Bron et al., J. Mol. Biol. 287, 117 (1999).
CAS Name: Teicoplanin A2
Additional Names: teichomycin A2Trademarks: Targocid (Aventis); Targosid (Aventis)
Literature References: Glycopeptide antibiotic complex produced by Actinoplanes teichomyceticus nov. sp.; structurally related to vancomycin, q.v. Comprised of 5 major components differentiated by a specific fatty acid moiety. Inhibits peptidoglycan synthesis in the cell wall of gram-positive bacteria. Isoln: BE 839259; C. Coronelli et al., US 4239751 (1976, 1980 both to Lepetit); F. Parenti et al., J. Antibiot. 31, 276 (1978); M. R. Bardone et al., ibid. 170. Separation of components: A. Borghi et al., DE 3320342; eidem, US 4542018 (1983, 1985 both to Lepetit); eidem, J. Antibiot. 37, 615 (1984). Structural studies: C. Coronelli et al., ibid. 621; J. C. J. Barna et al., J. Am. Chem. Soc. 106, 4895 (1984). Comparative in vitro activity: M. H. Cynamon, P. A. Granato, Antimicrob. Agents Chemother. 21, 504 (1982); H. C. Neu, P. Labthavikul, idem, 24, 425 (1983). Human pharmacokinetics: L. Verbist et al., ibid. 26, 881 (1984); P. L. Carver et al., ibid. 33, 82 (1989). Mechanism of action: S. Somma et al., ibid. 26, 917 (1984). Synergism with rifampin, q.v.: C. Watanakunakorn, J. Antimicrob. Chemother. 19, 439 (1987). HPLC determn in human serum: J. Levy et al., ibid. 533. Clinical trial in gram-positive bacterial infections: Y. Glupczynski et al., Antimicrob. Agents Chemother. 29, 52 (1986). Brief review: A. H. Williams, R. N. Grüneberg, J. Antimicrob. Chemother. 14, 441 (1984). Symposium on chemistry, pharmacology, activity, and clinical trials: J. Hosp. Infect. 7, Suppl. A, 47-112 (1986).
Trademarks: Ristomycin; Spontin; Riston
Literature References: Glycopeptide antibiotic complex produced by the actinomycete Nocardia lurida. Ristocetin A and the more active ristocetin B differ in the number of glucose, mannose, rhamnose and D-arabinose groups in their side chains. Isoln, crystallizn and chemical properties: J. E. Philip et al., Antibiot. Annu. 1956-57, p 699; eidem, US 2990329 (1961 to Abbott). Total structure determn of ristocetin A: D. H. Williams et al., Chem. Commun. 1979, 906; J. R. Kalman, D. H. Williams, J. Am. Chem. Soc. 102, 897 (1980). Identity of ristocetin A with ristomycin A: D. H. Williams et al., J. Chem. Soc. Perkin Trans. 1 1979, 787. 13C-NMR studies: F. Sztaricskai et al., Tetrahedron Lett. 21, 2983 (1980); M. P. Williamson, D. H. Williams, J. Chem. Soc. Perkin Trans. 1 1981, 1483. Revised configuration: C. M. Harris, T. M. Harris, J. Am. Chem. Soc. 104, 363 (1982). Biosynthesis: S. J. Hammond et al., Chem. Commun. 1983, 116. Tool for investigation of platelet aggregation: Howard, Firkin, Thromb. Diath. Haemorrh. 26, 362 (1971). Review: D. C. Jordan, Antibiotics vol. 1, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 84-89.
Additional Names: TSH; thyroid-stimulating hormone; thyrotropic hormone
Literature References: Glycoprotein hormone secreted by the anterior pituitary under the regulation of TRH, q.v. Stimulates the uptake of iodine, synthesis of thyroglobulin and release of thyroxine, q.v., by the thyroid. Structure is a heterodimer of a- and b- subunits; analogous with chorionic gonadotropin, luteinizing hormone, and follicle-stimulating hormone, q.q.v. Reviews of early literature: W. T. Salter, Hormones 2, 301-349 (1950); M. Sonnenberg, Vitam. Horm. 16, 205-261 (1958). Purification from bovine pituitaries: T.-H. Liao et al., J. Biol. Chem. 244, 6458 (1969). Amino acid sequence of bovine TSH: B. Shome et al., ibid. 246, 833 (1971); T.-H. Liao, J. G. Pierce, ibid. 850; of human a and b subunits: J. G. Pierce et al., Recent Prog. Horm. Res. 27, 165 (1971). Use in diagnosis of thyroid function: C. W. H. Havard, M. Boss, Br. Med. J. 3, 678 (1974). Review of structure and bioactivity: J. A. Magner, Endocr. Rev. 11, 354-385 (1990); and therapeutic potential: M. Grossmann et al., ibid. 18, 476-501 (1997).
Additional Names: Erythropoiesis stimulating factor; hemopoietine; ESF; Ep; Epo
Literature References: Glycoprotein hormone which stimulates red blood cell formation in higher organisms: P. Carnot, C. Deflandre, Compt. Rend. 143, 384 (1906). Single chain, 165 amino acid polypeptide containing approx 40% carbohydrate. Produced in response to hypoxia, primarily in the kidneys and to a lesser extent in the liver. Occurs normally in low concentrations in plasma; elevated levels in urine and plasma under conditions of anemic or hypoxic stress. Isoln from sheep plasma: W. F. White et al., Recent Prog. Horm. Res. 16, 219 (1960); from human urine: J. Espada, A. Gutnisky, Biochem. Med. 3, 475 (1970). Purification from human urine: T. Miyake et al., J. Biol. Chem. 252, 5558 (1977). Amino acid sequence: P.-H. Lai et al., J. Biol. Chem. 261, 3116 (1986). Biogenesis and control of production: J. W. Fisher, Proc. Soc. Exp. Biol. Med. 173, 289 (1983). Production by recombinant DNA technology in E. coli: S. Lee-Huang, Proc. Natl. Acad. Sci. USA 81, 2708 (1984); in mammalian cells: K. Jacobs et al., Nature 313, 806 (1985); F.-K. Lin et al., Proc. Natl. Acad. Sci. USA 82, 7580 (1985). Review of chemistry, pharmacology and clinical efficacy of recombinant human Epo (rHuEpo): K. K. Flaharty et al., Clin. Pharm. 8, 769-782 (1989). Review of clinical screening methods and abuse potential in sports: G. Lippi, G. Guidi, Clin. Chem. Lab. Med. 38, 13-19 (2000). Review of clinical experience: K.-U. Eckardt, Nephrol. Dial. Transplant. 16, 1745-1749 (2001); D. H. Henry, Expert Opin. Pharmacother. 6, 295-310 (2005).
CAS Name: (3b,5b)-3-[(O-b-D-Glucopyranosyl-(1®6)-O-D-glucopyranosyl-(1®4)-6-deoxy-3-O-methyl-a-L-glucopyranosyl)oxy]-14-hydroxy-19-oxocard-20(22)-enolide
Percent Composition: C 57.79%, H 7.39%,...
Literature References: Glycoside isolated from Thevetia neriifolia Juss., Apocynaceae: Bloch et al., Helv. Chim. Acta 43, 652 (1960). Separation from thevetin B: Delalande, Baisse, US 3030355; US 3043829 (1962). Structure: K. Tori et al., Tetrahedron Lett. 1977, 717.
Additional Names: FSH; follitropin
Literature References: Gonadotropic hormone secreted by the anterior pituitary under the regulation of gonadotopin-releasing hormone and inhibin, q.q.v. In the female, FSH stimulates estrogen production by the granulosa cells of the ovary and induces maturation of the Graafian follicle. In the male, stimulates the Sertoli cells of the testes and promotes spermatogenesis. Glycoprotein with mol wt ~34 kDa; multiple isoforms exist. Structure is a heterodimer of noncovalently linked a and b subunits; analogous with LH, TSH and chorionic gonadotropin, q.q.v. Isoln from pituitary: H. L. Fevold et al., Endocrinology 26, 999 (1940); C. H. Li et al., Science 109, 445 (1949). Prepn of human FSH from pituitaries and from postmenopausal urine: P. Roos, Acta Endocrinol. 59, Suppl. 131, 1-93 (1968). Amino acid sequence of human FSH a-subunit: P. Rathnam, B. B. Saxena, J. Biol. Chem. 250, 6735 (1975); of human b-subunit: B. B. Saxena, P. Rathnam, ibid. 251, 993 (1976). Production in Chinese hamster ovary cells by recombinant DNA technology: J. L. Keene et al., J. Biol. Chem. 264, 4769 (1989). Characterization of isoforms: P. G. Stanton et al., Mol. Cell. Endocrinol. 125, 133 (1996). Review of structure, biosynthesis and receptor binding: J. G. Pierce, T. F. Parsons, Annu. Rev. Biochem. 50, 465-495 (1981). Review of role in spermatogenesis: R. I. McLachlan et al., J. Endocrinol. 148, 1-9 (1996); in ovarian function and clinical use: B. C. Fauser, A. M. Van Heusden, Endocr. Rev. 18, 71-106 (1997).
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