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structure: see text] As part of our ongoing anticancer vaccine program, we recently found that antibodies generated in response to the KH-1-KLH construct recognized not only KH-1 antigen but also the Lewis Y (Le(y)) antigen as well, with antibody titer levels much higher than those observed after immunization with individual Le(y)-KLH vaccine constructs. In an attempt to explore the structure-antigenic relationship of these carbohydrate epitopes, several analogues of both KH-1 and Le(y) were synthesized. A convergent synthetic approach to the analogues was designed on the basis of well-established glycal methodology, employing a minimum number of building blocks to generate competent antigens with high stereoselectivity and reasonable yield.


Maria K Spassova, William G Bornmann, Govindaswami Ragupathi, George Sukenick, Philip O Livingston, Samuel J Danishefsky. Synthesis of selected LeY and KH-1 analogues: a medicinal chemistry approach to vaccine optimization. The Journal of organic chemistry. 2005 Apr 29;70(9):3383-95

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PMID: 15844973

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