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note
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See Supporting Information for details.
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41
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12244302599
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note
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Though aspartimides are prone to open at either imide carbonyl center, it is extremely unlikely that such a side reaction could account for Β-peptide product corresponding to more than half of the starting glycosylamine. That the isolated yield here reflects a majority of the starting glycosylamine countermands the possibility that the product derives from nucleophilic (glycosylamine) aspartimide opening.
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note
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Solid-phase synthesis of this peptide met with difficulties that were overcome by using a pseudoproline dipeptide monomer; see Supporting Information for details.
-
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46
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note
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Solid-phase synthesis of this peptide met with difficulties that were overcome by using a pseudoproline dipeptide monomer; see Supporting Information for details.
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Chemical synthesis of glycopepfides offers the ability to introduce structural modifications for the purpose of understanding the role of stereochemistry in glycoconjugate recognition. Evaluation of such stereochemical issues will be reported in due course. The implications of such a point mutation on binding to high mannose lectins is but one example of a fascinating question that can now be answered.
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49
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