Synthesis of sphingosines

Details Synthesis of sphingosines Synthesis of sphingosines

1995-01-23

1996-01-30

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

549371, 549372, 549306, 549433, 549434, 549435, 549437, 549450, 549453, 549476, 564489, 564507, 552 10, 560196, 568845, C07C20942

Patent

active

054881668

ABSTRACT:
Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.

REFERENCES:
patent: 4937328 (1990-06-01), Schmidt et al.
patent: 5012000 (1991-04-01), Illig et al.
patent: 5068345 (1991-11-01), Illig et al.
patent: 5110987 (1992-05-01), Liotta et al.
patent: 5137919 (1992-08-01), Igarashi et al.
patent: 5151360 (1992-09-01), Handa et al.
patent: 5200516 (1993-04-01), Hudlicky
patent: 5220043 (1993-06-01), Dong et al.
Newman, H., "A Stereoselective Synthesis of D-erythro-Sphingosine", Journal of the American Chemical Society, vol. 95, No. 12, pp. 4098-4099 (1973).
Raymond Boutin and Henry Rapoport, ".alpha.-Amino Acid Derivatives as Chiral Educts for Asymmetric Products. Synthesis of Sphingosine from .alpha.'-Amino-.alpha.,.beta.-ynones", Journal of Organic Chemistry, vol. 51, pp. 5320-5327 (1986).
Robin Polt, Matt A. Peterson and Lynn DeYoung, "Aluminoxy Acetals from .alpha.-Amino Esters: Chirality Transfer via Sequential Addition of Hydride and C-Nucleophiles. 2-Amino Alcohols and Sphingosines", Journal of Organic Chemistry, vol. 57, No. 20, pp. 5469-5480 (1992).
Peter Herold, "Synthesis of D-erythro and D-threo-Sphingosine Derivatives from L-Serine", Helvetica Chimica Acta, vol. 71, pp. 354-361 (1988).
Sanjay Nimkar et al., "A Stereoselective Synthesis of Sphingosine, A Protein Kinase C Inhibitor", Tetrahedron Letters, vol. 29, No. 25, pp. 3037-3040 (1988).
Mark A. Findeis and George M. Whitesides, "Fumarase-Catalyzed Synthesis of L-threo-Chloromalic Acid and Its Conversion to 2-Deoxy-D-ribose and D-erythro-Sphingosine", Journal of Organic Chemistry, vol. 52, 2838-2848 (1987).
Peter Zimmermann and Richard R. Schmidt, "Synthese von erythro-Spingosinen uber die Azidoderivate", Liebigs Annalyitical Chemistry, pp. 663-667 (1988). (English abstract).
Michio Obayashi and Manfred Schlosser, "An Efficient Synthesis of (2S,3R)- And (2S,3S)-Sphingosine", Chemistry Letters, pp. 1715-1718 (1985).
D. T. Gibson, M. Hensley, H. Yoshioka, and T. J. Mabry, "Formation of (+)-cis-2,3-Dihydroxy-1-methylcyclohexa-4,6-diene from Toluene by Pseudomonas putida", Biochemistry, pp. 1626-1630 (1970).
Tomas Hudlicky et al, "Biocatalysis as the Strategy of Choice in the Exhaustive Enantiomerically Controlled Synthesis of Conduritols", Journal of Chem. Soc. Perkin Trans. 1, pp. 2907-2917 (1991).
Tomas Hudlicky, Jacques Rouden and Hector Luna, "Rational Design of Aza Sugars via Biocatalysis: Mannojirimycin and Other Glycosidase Inhibitors", Journal of Organic Chemistry, vol. 58, No. 5, pp. 985-987 (1993).
Tomas Hudlicky, Hector Luna, John D. Price and Fan Rulin, "Microbial Oxidation of Choloroaromatics in the Enantiodivergent Synthesis of Pyrrolizidine Alkaloids: Trihydoxyheliotridanes", Journal of Organic Chemistry, vol. 55, pp. 4683-4687 (1990).
Tomas Hudlicky, Hector Luna, Gracieia Barbieri and Lawrence D. Kwart, "Enantioselective Synthesis through Microbial Oxidation of Arenes. 1. Efficient Preparation of Terpene and Prostanoid Synthons", Journal of American Chemical Society, vol. 110, pp. 4735-4741 (1988).
C. A. Grob and F. Gadient, "Die Synthesis des Sphingosins und seiner Steroisomeren", Helvetica Chimica Acta, vol. XL, No. 130, pp. 1145-1157 (1957) (English summary).
Gerben J. Zylstra and David T. Gibson, "Toluene Degradation by Pseudomonas putida F1", The Journal of Biological Chemistry, vol. 264, No. 25, pp. 14940-14946 (1989).
Elmer J. Reist and Pamela H. Christie, "Synthesis of trans-and cis-Sphingosine", Journal of Organic Chemistry, vol. 35, No. 12, pp. 4127-4130 (1970).
Peter Somfai and Roger Olsson, "An Enantiospecific Synthesis of D-erythro-Sphingosine from D-Tartaric Acid", Tetrahedron, vol. 49, No. 30, pp. 6645-6650 (1993).
Hirotaka Shibuya, Keiko Kawashima, Masahiko Ikeda and Isao Kitagawa, "Synthesis of Two Pairs of Enantiomeric C.sub.18 -Sphingosines", Tetrahedron Letters, vol. 30, No. 51, pp. 7205-7208 (1989).
Bruno Bernet and Andrea Vasella, "Enantioselective Synthesis of D-erythro-Sphingosine", Tetrahedron Letters, vol. 24, No. 49, pp. 5491-5494 (1993).
Kenji Mori and Yuji Funaki, "Synthesis of (4E,8E,2S,3R,2'R)-N-2'-Hydroxyhexadecanoyl-1-o-.beta.-D-Glucopyranosyl-9-m ethyl-4,8-Sphingadienine, the Fruiting-Inducing Cerebroside in a Basidiomycete Schizophyllum Commune", Tetrahedron, vol. 41, No. 12, pp. 2379-2386 (1985).
Peter Tkaczuk and Edward R. Thorton, "Useful Syntheses of erythro-and threo-N-Oleoyl-D-Sphingosines (Ceramides) and Galactosylceramides (Cerebrosides) from L-Serine", Journal of Organic Chemistry, 46, pp. 4393-4398 (1981).
Philip Garner, Jun Min Park and Elise Malecki, "A Stereodivergent Synthesis of D-erythro-Sphingosine and D-threo-Sphingosine from L-Serine", Journal of Organic Chemistry, vol. 53, pp. 4395-4398 (1988).
Julian N. Kanfer and Sen-itiroh Hakomori, "Sphingolipid Biochemistry", Handbook of Lipid Research, Ed. Donald J. Hanahan, Plenum Press, vol. 3, pp. 1-9 (1983).
Alfred H. Merrill, Jr. et al, "Structural Requirements for Long-Chain (Sphingoid) Base Inhibition of Protein Kinase C in Vitro and for the Cellular Effects of These Compounds", Biochemistry, vol. 28, pp. 3138-3145 (1989).
Herbert E. Carter et al, "Biochemistry of the Sphingolipides", Journal of Biological Chemistry, vol. 170, pp. 269-283 (1947).
Janet M. Harouse et al, "Inhibition of Entry of HIV-1 in Neural Cell Lines by Antibodies Against Galactosyl Ceramide", Science, vol. 253, pp. 320-323 (1991).
Alessandro Bongini et al, "Iodocyclofunctionalization of (Z)-1-Trichloroacetimidoyloxyalk-2-enes and 3-Trichloroacetimidoyloxyalk-1-enes. Synthesis (+)-erythro-Sphinganine Triacetate and (+)-threo-Sphinganine Triacetate", Journal of Chem. Soc. Perkin Trans. 1, pp. 1339-1344 (1986).
Herbert E. Carter et al, "Synthesis and Configuration of Dihydrosphingosine", Journal of American Chemical Society, vol. 75, pp. 1007-1008 (1953).
Tomas Hudlicky et al, "Biocatalysis as a Rational Approach to Enantiodivergent Synthesis of Highly Oxygenated Compounds: (+)- and (-)-Pinitol and Other Cyclitols", Israel Journal of Chemistry, vol. 31, pp. 229-238 (1991).
Tomas Hudlicky et al, "An Enantiodivergent Approach to D- and L-Erythrose via Microbial Oxidation of Chlorobenzene", Tetrahedron Letters, vol. 30., No. 31, pp. 4053-4054 (1989).
R. Schmidt et al, "Synthesis of D-erythro Sphingosines", vol. 27, No. 4, pp. 481-484 (1986).

Affiliated with

Also associated with

Rating

Synthesis of sphingosines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of sphingosines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of sphingosines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-157525