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Original Articles

Olefin Cross‐Metathesis: A Powerful Tool for Constructing Vaccines Composed of Multimeric Antigens

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Pages 425-440 | Received 24 Feb 2005, Accepted 18 Mar 2005, Published online: 16 Aug 2006

References and Notes

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  • Figure 4 was reproduced with slight modification from reference 9
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  • Zhan Catalyst I sold by Zanan Pharma Ltd
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  • Sutton , A. E. , Seigal , B. A. , Finnegan , D. F. and Snapper , M. L. 2002 . New tandem catalysis: preparation of cyclic enol ethers through a ruthenium‐catalyzed ring‐closing metathesis‐olefin isomerization sequence . J. Am. Chem. Soc. , 124 : 13390 – 13391 . To evaluate whether this impurity was responsible for the proliferation of our isomerization pathway we rigorously purified the catalyst according to the procedure described in the above paper. However, when subjected to the same reaction conditions as the unpurified Grubbs catalyst, the purified material led to similar levels of olefin isomerization product. For a recent review of nonmetathetic activity of the Grubbs catalyst, see: Alcaide, B.; Almendros, P. Non‐metathetic behavior patterns of Grubbs' carbene Chem. Eur. J. 2003, 9, 1258–1262.. Impurities in the commercial sample of Grubbs catalyst (3) is presumed to be responsible for olefin isomerization in some instances . Impurities in the commercial sample of Grubbs catalyst (3) is presumed to be responsible for olefin isomerization in some instances
  • Unpublished results
  • Cho , Y. S. , Wan , Q. and Danishefsky , S. J. 2005 . Large scale synthesis of peracetylated GM2 glycosylamino acid for preparation of a multiantigenic prostate cancer vaccine . Bioorg. Med. Chem. , in press
  • Unpublished results
  • Allen , J. R. , Allen , J. G. , Zhang , X. F. , Williams , L. J. , Zatoriski , A. , Ragupathi , G. , Livingston , P. O. and Danishefsky , S. J. 2000 . A second generation synthesis of the MBr1 (Globo‐H) breast tumor antigen: new application of the n‐pentenyl glycoside method for achieving complex carbohydrate protein linkages . Chem. Eur. J. , 6 : 1366 – 1375 .

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