Special Issues - Molecules - MDPI

Peptide synthesis has been developed into one of the most efficient synthetic procedures in organic chemistry. The problems of orthogonal functional group protection and amide bond formation without racemization have been developed in a number of ingenious strategies. Optimization, in particular, has been achieved in stepwise solid phase synthesis. This in turn made possible the development of combinatorial synthesis allowing the synthesis of millions of peptide compounds of high purity in a few days. A variety of methodologies and strategies have been developed and continue to be developed to determine structures and to evaluate peptides and peptidomimetics. The development of methods for solid phase synthesis of a variety of organic and inorganic structures using similar strategies as in peptide synthesis are being vigorously pursued. However, existing instrumentation and technology is not sufficient to cover current demands for peptides, and thus new approaches and technologies for cost-effective synthesis of peptide arrays are needed.

Molecules, an international, peer-reviewed Open Access journal.

N2 - Peptide synthesis has been developed into one of the most efficient synthetic procedures in organic chemistry. The problems of orthogonal functional group protection and amide bond formation without racemization have been developed in a number of ingenious strategies. Optimization, in particular, has been achieved in stepwise solid phase synthesis. This in turn made possible the development of combinatorial synthesis allowing the synthesis of millions of peptide compounds of high purity in a few days. A variety of methodologies and strategies have been developed and continue to be developed to determine structures and to evaluate peptides and peptidomimetics. The development of methods for solid phase synthesis of a variety of organic and inorganic structures using similar strategies as in peptide synthesis are being vigorously pursued. However, existing instrumentation and technology is not sufficient to cover current demands for peptides, and thus new approaches and technologies for cost-effective synthesis of peptide arrays are needed.


Amos Smith Research Group - Penn Arts & Sciences

14/03/2014 · Trabocchi, A. and Guarna, A. (2014) Peptoids, in Peptidomimetics in Organic and Medicinal Chemistry: The Art of Transforming Peptides in …

One of the key elements in solid phase chemistry is the polymeric resin. Since the introduction of the Merrifield resin, libraries of peptides, nucleotides, and organic molecules have been generated on solid supports. Many of the resins that are currently employed as supports were originally developed for the synthesis of peptides. Polar functionalities such as carboxylic acids and amides were released upon cleavage of products from the resins. Recent advances in linker technology have allowed other polar functional groups, such as alcohols and thiols, also to be attached to the polymer support. In fact, most of the linkers available for solid support synthesis to date require polar functional groups for binding, and the same polar groups are released after cleavage. To generate libraries with biological activity, however, such polar functionalities may possess unfavorable pharmacological properties. Because of poor oral bioavailability and enzymatic degradation of linear peptides, modified peptides, peptidomimetics, and cyclic peptides have become appealing targets for the design of therapeutic agents with increased pharmacological activities. Therefore, we directed our attention to the design of new solid support linkers for non-polar or aromatic compounds that are commonly found in medicinally important agents.