Cyclo-tetrapeptides are useful intermediates in drug design. This could be attributed to the specific characteristics of cyclo-tetrapeptides such as their low molecular weight, and favorable pharmacokinetic properties, as well as their ability to support a wide range of substituents and functional groups. Even though, cyclo-tetrapeptides could potentially be used for various pharmaceutical and industrial applications, their applications are currently limited because of the problems in their synthesis. The main problem for their synthesis is the difficulty in bringing the two termini in a linear tetrapeptide sufficiently close to each other for the cyclization to occur, which would lead to ineffective cyclization. Such steric and conformational hindrance issues are due to peptide bonds in trans conformation, and the tendency of linear peptides to exist in more extended.Utilizing a Pd-catalyzed tandem-deprotection-cyclization reaction, we have developed a novel methodology to synthetize symmetrical and unsymmetrical cyclic tetrapeptides, from open-chain N-cbz-dipeptidobenzotriazolides. The cyclo-oligomerization reactions were successfully carried out with dipeptidobenzotriazoles as the starting materials, yielding cyclo-tetrapeptides. The cyclo-tetrapeptides cannot be prepared efficiently by previously reported synthesis methods. This novel methodology would provide a convenient means for synthesis of a wide variety of cyclo-tetrapeptides that could potentially have applications in the pharmaceutical industry, catalysis, and material sciences.

Cyclo-dimerization approach in the synthesis of C<sub>2 </sub>symmetric cyclo-tetrapeptides

247th National Meeting (2014)

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Cyclo-dimerization approach in the synthesis of C2 symmetric cyclo-tetrapeptides

Cyclo-dimerization approach in the synthesis of C₂symmetric cyclo-tetrapeptides