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Volumn 36, Issue 2, 1996, Pages 185-193

α-multistriatin: The first total synthesis of a natural product via antibody catalysis

(2)  Sinha, Subhash C a   Keinan, Ehud a  

a NONE

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Indexed keywords


EID: 0039564359     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijch.199600025     Document Type: Article
Times cited : (7)

References (58)
  • 12
    • 0039495882 scopus 로고    scopus 로고
    • note
    • As all reagents used in the synthesis are achiral, the only source of asymmetry in the molecule is the antibody-catalyzed reaction. The other three asymmetric centers are produced later by chirality transfer where only the relative stereochemistry is controlled.
  • 19
  • 39
    • 0038903217 scopus 로고    scopus 로고
    • note
    • Assay conditions: antibody (0.5 μM), substrate (50-500 μM), 1,3-bis[tris(hydroxymethyl) methylamino]propane-buffered saline (50 mM, pH 6.5, 50 mM NaCl). All reactions were carried out at 24 °C and monitored at 254 nm by RP-HPLC (Hitachi L-6200A equipped with a Spherisorb column (25 cm × 4.6 mm, C18, 5 μm) using 42:58 acetonitrile:water at 0.8 mL/min.
  • 40
    • 0038903218 scopus 로고    scopus 로고
    • note
    • In one experiment, a mixture of all four compounds, 9a-d, was subjected to antibody-catalyzed hydrolysis, resulting in complete, selective consumption of 9a with essentially no change in the concentration of 9b and small decrease of 9c,d. However, since enol ethers 9c,d are hydrolyzed approximately ten times faster than 9a,b under the same buffer conditions, in order to achieve high ee and avoid contamination of the product by racemic 5, it was necessary to remove 9b-d from the mixture before the antibody-catalyzed step.
  • 44
    • 33751385567 scopus 로고
    • (d) Shin, I.; Zhou, H.-Q.; Que, N.L.S.; Liu, H.-W. Swedenborg, P.D.; Jones, R.L. J. Org. Chem. 1993, 58, 2923. The absolute configuration at the homobenzylic position was assigned on the basis of the many examples reported by Evans, including a closely related asymmetric alkylation reaction with unsubstituted benzyl bromide.
    • (1993) J. Org. Chem. , vol.58 , pp. 2923
    • Shin, I.1    Zhou, H.-Q.2    Que, N.L.S.3    Liu, H.-W.4    Swedenborg, P.D.5    Jones, R.L.6
  • 45
    • 0016756272 scopus 로고
    • Antibody 14D9 is the product of a murine hybridoma cell line. It is made by producing ascites fluid from this cell line followed by ammonium sulfate precipitation, anion exchange, and affinity chromatography with immobilized G protein: (a) Köhler, G.; Milstein, C. Nature 1975, 256, 495.
    • (1975) Nature , vol.256 , pp. 495
    • Köhler, G.1    Milstein, C.2
  • 48
    • 0024382916 scopus 로고
    • (b) Wong, C.-H. Science 1989, 244, 1145.
    • (1989) Science , vol.244 , pp. 1145
    • Wong, C.-H.1
  • 49
  • 55
    • 0000221693 scopus 로고
    • The closest literature precedents involve enantioselective protonation of various metal enolates. See, for example: (a) Fehr, C.; Galindo, J. J. Am. Chem. Soc. 1988, 110, 6909.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6909
    • Fehr, C.1    Galindo, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.