Method for producing marine-derived compounds and novel compound

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing at least three carbocyclic rings

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435146, 435148, 435183, 435189, 435190, C12P 1500, C12P 742, C12P 726

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active

060460415

ABSTRACT:
A fortified enzyme preparation of the gorgonian Pseudopterogorgia americana or Pseudopterogorgia elisabethae has been developed which efficiently transforms a variety of precursor molecules, e.g., sterols, to their corresponding metabolites, e.g., 9(11)-secosteroid in high yield. NAD, NADP, and glutamate dehydrogenase can be used as additives in this enzymatic conversion. In addition to naturally-occurring metabolites, novel secosteroids have been prepared.

REFERENCES:
patent: 5783431 (1998-07-01), Peterson et al.
D'Auria, M.V., L.. Minale, R. Riccio (1993) "Isolation and Synthesis of a New 9.11-Secosterol From The Sponge Spongia Officinalis", Journal of Natural Products 57(9):1200-1226.
He, Haiyin et al. (1995) "New Antiproliferative And Antinflammatory 9, 11-Secosterols From The Gorgonian Pseudopterogoria sp." Tetrahedron Letters 51(1):51-58.
D'Auria, Maria Valeria, Luigi Minale and Raffaele Riccio (1993) "Polyoxgenated Steroids of Marine Origin" Chem. Rev. 93:1839-1895.
Ochi, M. et al. (1991) "Calicoferols A and B, Two Novel Secosterols Possessing Brine-Shrimp Lethality from the Gorgonian Calicogorgia sp." Chemistry Letters, pp. 427-430.
Brown, S. and Kelly, R. (1993) "Characterization of Amylolytic Enzymes, Having Both .alpha.-1,4 and .alpha.-1,6 Hydrolic Activity, From The Thermophilic Archaea Pyrococcus furiosus and Thermococcus litoralis" Applied and Environmental Microbiology Rev. 59(8):2614-2621.
Miller, S. et al. (1995) "9,11-Seco-24-Hydroxydinosterol From Pseudopterogorgia Americana" Tetrahedron Letters 36(8):1227-1228.
Migliulo, A. et al. (1991) "Structure Elucidation and Synthesis of 3.beta.,6.alpha.-Dihydroxy-9-oxo-9,11-Seco-5.alpha.-Cholest-7-en-11-al, a Novel 9,11-Secosterol From The Sponge Spongia Officinalis" Tetrahedron Letters 47(37):7937-7950.
Kerr, R. et al. (1991) "Biosynethetic Studies of Marine Lipids. 38..sup.1 Mechanism and Scope of Sterol Side Chain Dealkylation in Sponges: Evidence for Concurrent Alklyation and Dealkylation" J. Am. Chem. Soc. 114:299-303.
Kerr, R. et al. (1996) "A Chemoenzymatic Synthesis of 9(11)-Secosteroids using an Enzyme Extract of the Marine Gorgonian Pseudopterogorgia americana" Tetrahedron Letters 37(46):8301-8304.

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