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Journal of Central South University of Technology

, Volume 12, Issue 6, pp 693–698 | Cite as

Synthesis of o-L-α-glycerylphosphoryl-L-serine

  • Tang Rui-ren Email author
  • Yan Zi-er 
  • Luo Yi-ming 
Article

Abstract

A new efficient method for preparing o-L-α-glycerylphosphoryl-L-serine was presented. D-α, β-isopropylidene glycerol was phosphorylated with phenylphosphoryl dichloride and the resulting o-D-α,β-isopropylidene glycerylphenylphosphoryl chloride was esterified with N-tert-butoxycarbonyl-L-serine ethyl ester in the presence of pyridine to give acetone L-α-glycerylphenylphosphoryl-N-tert-butoxycarbonyl-L-serine ethyl ester. Finally, the protective groups were removed by two-step hydrolysis while strictly controlling pH value. The reaction to produce (1, 2), (5, 6)-diisopropylidene-D-mannitol, which is the key precursor for the preparation of D-α, β-isopropylidene glycerol, was monitored by using gas chromatography-mass spectrometer in order to obtain an optimum yield of 65%. All compounds were characterized through elemental analysis, infrared spectra, 1H, 13C, 31P-nuclear magnetic resonance spectra and mass spectra.

Key words

o-L-α-glycerylphosphoryl-L-serine N-tert-butoxycarbonyl-L-serine ethyl ester D-α, β-isopropylidene glycerol 

CLC number

O629.12 

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References

  1. [1]
    Florence T, Véronique S, Francois J R. Another link between phospholipid transmembrane migration and ABC transporter gene family, inferred from a rare inherited disorder of phosphatidylserine externalization [J]. Biochemical and Biophysical Research Communications, 1997, 214(2): 548–552.Google Scholar
  2. [2]
    Pepen E. Phylogenetic Aspects, Central and Peripheral Synapses, Clinical Significance [M]. New York: Cholinergic Mechanism, Plenum Publishing Co, 1981.Google Scholar
  3. [3]
    Camillom P, Carlo S. Pharmaceutical Compositions for the Therapy of Involutive Cerebral Syndromes [P]. US, 4950776. 1990-08-21.Google Scholar
  4. [4]
    Baer E, Buchnea D, Stancer H C. Synthesis of L-α-glycerylphosphoryl-L-serine [J]. Journal of American Chemical Society, 1959, 81(3): 2166–2169.CrossRefGoogle Scholar
  5. [5]
    Wray S, Wilkie D R. The relationship between plasma urea levels and some muscletrimethylamine levels in xenopus laevis: a 31P and 14N nuclear magnetic resonance study [J]. The Journal of Experimental Biology, 1995, 198(2): 373–378.Google Scholar
  6. [6]
    Yin X H. Phase transfer catalyzed synthesis of D-dropropizine with D-mannitol as starting material [J]. Chemical Reagents, 2001, 23(6): 349–350.Google Scholar
  7. [7]
    Huang P Q, Wu T J. A flexible approach to the γ-amino-β-hydroxy acid moiety of hapalosin [J]. Chinese Journal of Chemistry, 2003, 21(7): 723–726.CrossRefGoogle Scholar
  8. [8]
    Adamson G, Blaskovich M A. Simple and convenient synthesis of tert-butyl esters of fmoc-serine, fmocthreonine, and fmoc-tyrosine [J]. Journal of Organic Chemistry, 1991, 56(10): 3447–3449.CrossRefGoogle Scholar
  9. [9]
    Kuttan A, Nowshudin S, Rao M N A. Ceric ammonium nitrate (CAN) mediated esterification of N-BOC amino acids allows either retention or removal of the N-BOC group [J]. Tetrahedron Letters, 2004, 45 (12): 2663–2665.CrossRefGoogle Scholar
  10. [10]
    Bush S M, North M, Sellarajah S. Synthesis and chiro-optical properties of copolymers from N-BOC-O-methacryloyl-(S)-serine benzhydryl ester and methyl methacrylate [J]. Polymer, 1998, 39(13): 2991–2993.CrossRefGoogle Scholar
  11. [11]
    James K D, Ellington A D. The use of aluminum chloride for removal of BOC groups on 5′-amino-2′, 5′-dideoxyoligonucleotides during solid-phase synthesis [J]. Tetrahedron Letters, 1998, 39(3): 175–178.CrossRefGoogle Scholar
  12. [12]
    Kuszmann J, Tomori E. The acetalation of D-mannitol part III: a detail study of the acetalation of D-mannitol with acetone-sulfuric acid [J]. Carbohydr Res, 1985, 137: 276–281.CrossRefGoogle Scholar
  13. [13]
    Kinnunen P K, Schroder T M, Virtanen J A. Process for Preparing 1, 2-diacyl-Sn-glycerols [P]. US, 4360694. 1981-04-06.Google Scholar
  14. [14]
    Otaka A, Miyoshi K, Terrence R, et al. Synthesis and application of N-BOC-L-2-amino-4-(diethylphosphono)-4,4-difluorobutanoic acid for solid-phase synthesis of nonhydrolyzable phosphoserine peptide analogues[J]. Tetrahedron Letters, 1995, 36(6): 927–930.CrossRefGoogle Scholar

Copyright information

© Central South University 2005

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina

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