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The use of azide and alkyne connecting groups avoids certain protecting group problems commonly encountered in solid phase peptide synthesis. For example, orthogonal protection was required for an aspartate residue of resin-3 to prepare for cyclization by amide bond formation. The 4-(N-(1-(4,4-dimethyl-2, 6-dioxocyclohexylidene)-3-methylbutyl)amino)benzyl ester (Dmab) group, most commonly used in such situations, is expensive, bulky, and chemically sensitive: T. Johnson, M. Liley, T. J. Cheeseright, F. Begum, J. Chem. Soc. Perkin Trans. 1 2000, 2811-2820. The introduction and manipulation of aspartate can give rise to undesired aspartamide cyclization with neighboring residues during both Fmoc and Boc synthetic approaches and piperidide formation during Fmoc manipulations; deprotection is often relatively difficult. The standard solutions to these difficulties (such as protecting the preceding residue as N-Hmb; Hmb = 2-hydroxy-4-methoxybenzyl) are also somewhat cumbersome. Each of these problems were encountered in the synthesis and isolation of cyclo-3, but did not occur in the preparation and reactions of the analogous sequence 1.
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