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The vaccine conjugate was administered and used under an IND (investigational new drug) protocol with the Food and Drug Administration (USA) held by the Memorial Sloan-Kettering Cancer Center.
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To date, we are in the position where we can synthesize fully deprotected allyl glycoside 40 on a gram scale with minimal complications.
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Synthetic compound 100 was conjugated to KLH using m-maleimidobenzoyl-N-hydroxysuccinamide ester (MBS), a heterobifunctional reagent which cross-links thiol groups with amino groups.
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Mono-and diclusters of the TF antigen have been reported: H. Kunz, S. Birnbach, P. Wering, Carbohydr. Res. 1990, 202, 207.
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Conditions including pH10 aq. NaOH/MeOH, LiOH, LiOOH, and cat. NaOMe/MeOH failed to remove the three benzoates.
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