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Volumn 72, Issue 5, 2007, Pages 1691-1698

A new synthesis of lysophosphatidylcholines and related derivatives. Use of p-toluenesulfonate for hydroxyl group protection

Author keywords

[No Author keywords available]

Indexed keywords

LYSOPHOSPHATIDYLCHOLINES; LYSOPHOSPHOLIPID MOLECULES;

EID: 33847661931     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062352f     Document Type: Article
Times cited : (16)

References (41)
  • 1
    • 35449004614 scopus 로고    scopus 로고
    • 4th ed, Vance, D. E, Vance J. E, Eds, Eisevier Science: Amsterdam
    • McPhail, L. In Biochemistry of Lipids, Lipoproteins and Membranes, 4th ed.; Vance, D. E., Vance J. E., Eds.; Eisevier Science: Amsterdam, 2002; pp 315-340.
    • (2002) Biochemistry of Lipids, Lipoproteins and Membranes , pp. 315-340
    • McPhail, L.1
  • 6
    • 0032549176 scopus 로고    scopus 로고
    • Wong, J. T.; Tran, K.; Pierce, G. N.; Chan, A. C.; O, K.; Choy, P. C. J. Biol. Chem. 1998, 273, 6830-6836.
    • Wong, J. T.; Tran, K.; Pierce, G. N.; Chan, A. C.; O, K.; Choy, P. C. J. Biol. Chem. 1998, 273, 6830-6836.
  • 16
    • 0346158367 scopus 로고    scopus 로고
    • Van Leeuwen, F. N.; Giepmans, B. N. G.; Van, Meeteren, L. A.; Moolenaar, W. H. Biochem. Soc. Trans. 2003, 31, 1209-1212.
    • (a) Van Leeuwen, F. N.; Giepmans, B. N. G.; Van, Meeteren, L. A.; Moolenaar, W. H. Biochem. Soc. Trans. 2003, 31, 1209-1212.
  • 28
    • 0033617412 scopus 로고    scopus 로고
    • The low yield clearly results from hydrolysis of both ester groups. These groups have shown quite similar reactivities in reaction with a series of base catalysts that were used in an attempt to achieve chemoselective cleavage (via base-catalyzed elimination) of the acetyl group. Along these lines both DBU and Verkade's Superbase (Ilancumaran, P.; Verkade, J. G. J. Org. Chem. 1999, 64, 3086-3089) failed to improve the yield of compound 10.
    • The low yield clearly results from hydrolysis of both ester groups. These groups have shown quite similar reactivities in reaction with a series of base catalysts that were used in an attempt to achieve chemoselective cleavage (via base-catalyzed elimination) of the acetyl group. Along these lines both DBU and Verkade's Superbase (Ilancumaran, P.; Verkade, J. G. J. Org. Chem. 1999, 64, 3086-3089) failed to improve the yield of compound 10.
  • 29
    • 0001755181 scopus 로고    scopus 로고
    • We have found that the combination of tert-butylamine/methanol gives better results than the methods previously used for hydrolysis of methoxyacetyl esters, including catalysis with ytterbium(III) triflate: Hanamoto, T, Sugimoto, Y, Yokoyama, Y, Inanaga, J. J. Org. Chem. 1996, 61, 4491-4492
    • We have found that the combination of tert-butylamine/methanol gives better results than the methods previously used for hydrolysis of methoxyacetyl esters, including catalysis with ytterbium(III) triflate: Hanamoto, T.; Sugimoto, Y.; Yokoyama, Y.; Inanaga, J. J. Org. Chem. 1996, 61, 4491-4492.
  • 40
    • 33847636412 scopus 로고    scopus 로고
    • The reaction conditions that have been reported for acylation of lysophosphatidylcholines generally required a large (5- to 10-fold) excess of acylating agent; see ref 18a,b for detailed discussion
    • The reaction conditions that have been reported for acylation of lysophosphatidylcholines generally required a large (5- to 10-fold) excess of acylating agent; see ref 18a,b for detailed discussion.
  • 41
    • 0032741250 scopus 로고    scopus 로고
    • Compound 17 was completely hydrolyzed by phospholipase A2 from bee venom to give lysophosphatidylcholine 12b and 12-N-(5′- dimethylaminonaphthalene-1′-sulfonyl)aminododecanoic acid under the assay conditions previously reported: Roodsari, F. S.; Wu, D.; Pum, G. S.; Hajdu, J. J. Org. Chem. 1999, 64, 7727-7737.
    • Compound 17 was completely hydrolyzed by phospholipase A2 from bee venom to give lysophosphatidylcholine 12b and 12-N-(5′- dimethylaminonaphthalene-1′-sulfonyl)aminododecanoic acid under the assay conditions previously reported: Roodsari, F. S.; Wu, D.; Pum, G. S.; Hajdu, J. J. Org. Chem. 1999, 64, 7727-7737.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.