New applications of the n-pentenyl glycoside method in the synthesis and immunoconjugation of fucosyl GM1: A highly tumor-specific antigen associated with small cell lung carcinoma

Journal of the American Chemical Society

Volumn 121, Issue 47, 1999, Pages 10875-10882

  Allen, Jennifer R ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; GLYCOSIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; GLYCOPROTEIN SYNTHESIS; LUNG SMALL CELL CANCER; STEREOSPECIFICITY; VACCINATION;

EID: 0033485771     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992594f     Document Type: Article

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53. We note that this is not a general result in using highly advanced glycals. For example, analogous deprotection steps have been accomplished with the hexasaccharide glycal corresponding to Globo-H and the non-asaccharide glycal corresponding to the KH-1 antigen (see ref 9 for a review). This appears to be the only case thus far where we have been unable to affect such conversions, pointing to perhaps the sensitivity of the sialic acid and glycal units in this particular structure.
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71. For a typical procedure, see: (a) Lloyd, K. O.; Savage, A. Glycoconjugate J. 1991, 8, 439. (b) Hardy, M. R.; Townsend, R. R. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 3289.
72. The yields of carbohydrate conjugates are similar for both the allyl linker and the pentenyl linker. The incorporation of ∼300 carbohydrates per molecule of carrier protein is what was expected based on results using the allyl glycoside of Globo-H.
73. Allen, J. R.; Allen, J. G.; Zhang, X.-F.; Williams, L. J.; Zatorski, A.; Danishefsky, S. J. Eur. J. Chem., in press.
74. Please see attached Supporting Information for general experimental procedures.