2014
DOI: 10.1002/chem.201304262
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Tandem Deprotection–Dimerization–Macrocyclization Route to C2 Symmetric cyclo‐Tetrapeptides

Abstract: Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo-dimerization from readily available Cbz-dipeptidoyl benzotriaz… Show more

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Cited by 13 publications
(8 citation statements)
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“…275 11. TANDEM DEPROTECTION−DIMERIZATION−MACROCYCLI-ZATION Ha et al 277 designed a procedure they refer to as "tandem deprotection−dimerization−macrocyclization" in which the Nterminally Cbz protected dipeptides were preactivated as the respective benzotriazolides (Scheme 17). The activated precursor was then deprotected and cyclized in a single step, resulting in dimerization and subsequent cyclization to yield a variety of C 2 symmetric CTPs in yields ranging 22−86%.…”
Section: -Membered Ctpsmentioning
confidence: 99%
“…275 11. TANDEM DEPROTECTION−DIMERIZATION−MACROCYCLI-ZATION Ha et al 277 designed a procedure they refer to as "tandem deprotection−dimerization−macrocyclization" in which the Nterminally Cbz protected dipeptides were preactivated as the respective benzotriazolides (Scheme 17). The activated precursor was then deprotected and cyclized in a single step, resulting in dimerization and subsequent cyclization to yield a variety of C 2 symmetric CTPs in yields ranging 22−86%.…”
Section: -Membered Ctpsmentioning
confidence: 99%
“…The synthesis of cyclic peptides is often challenging. Benzotriazole methodology was extended to use in the synthesis of various cyclic peptides via dimerization macrocyclization approach [19] Figure [4][5][6].…”
Section: Benzotriazole In Cyclic Peptide Synthesismentioning
confidence: 99%
“…Reports on the successful preparation of cyclotetrapeptides containing a combination of αand β-amino acids using the metal template strategy can be found in the literature, which further substantiates the difficulty experienced when synthesising 12-membered cycles compared to 13-or 14-membered ring analogues. 63,64 For example, a Pd-promoted tandem deprotection/cyclisation dimerization method was used to prepare C 2 symmetrical cyclotetrapeptides from N-Cbz-dipeptidoyl benzotriazole (Bt) sequences (Cbz = carboxybenzyloxy) containing either βor αand β-amino acids (Scheme 8). 50 Tetrapeptides, linear or cyclic, were used to create molecularly imprinted cavities in polymer-cellulose composites.…”
Section: Organic and Biomolecular Chemistry Reviewmentioning
confidence: 99%