Peptide nucleic acids chemical synthesis

In addition, Dose and Seitz (2005) employed native chemical ligation to synthesize peptide nucleic acids (PNAs) by linking shorter segments of PNAs to make long contiguous strands, which could not be made through typical oligo synthesis procedures. 

Dose, C., and Seitz, O. (2005) Convergent synthesis of peptide nucleic acids by native chemical ligation. Org. Lett. 7(20), 4365-4368. 

Structure, properties, application, strategy, and practice of chemical synthesis of peptide-nucleic acids 02UK81. 

In collaboration with Eckard Wimmer (State University of New York, Stony Brook, New York) a breakthrough in our understanding of the replication mechanism of the poliovirus was achieved. Key to this study proved to be the accessibility of homogeneous uridylylated oligopeptide fragments. In itself, the chemical synthesis of peptide nucleic acid fragments of the complexity required for these studies, with the many synthetic hurdles that are caused by the incompatibility of standard peptide synthesis and nucleic acid synthesis protocols, represents a milestone in the oeuvre of Jacques van Boom and a hallmark in bioorganic chemistry. 

Sun and coworkers have chemically attached poly(propionylethylenimine-co-ethyleni-mine), which is a widely used aminopolymer in peptide synthesis, to the acid-oxidation-induced carboxylic acid groups on CNTs via diimide-activated amidation with EDAC under ambient conditions. Various biomolecules, including DNA, PNA (peptide nucleic acid), and proteins, have also been successfully coupled to the acid-oxidized CNTs through the carboxylic acid functional linkers. 

More exotic alternatives to nucleosides have been proposed based on the peptide nucleic acid (PNA) analogues of Nielsen and coworkers (93). Miller and coworkers (94) were able to demonstrate the facile prebiotic synthesis of all of the components of PNA under the same chemical conditions required for the synthesis of the purines or pyrimidines. Nevertheless there are maity alternative structures, which have not yet been investigated. 

FIGURE 10 Structure of peptide nucleic acid (PNA). An artificial oligomer produced by chemical synthesis retains the ability to pair with bases, but is resistant to degradation by nucleases because its backbone does not contain the normal phosphodiester linkage. 

The application of solid-phase synthesis and automation has revolutionized much of the chemical and biochemical research related to peptides and nucleic acids.5 Thus, it is likely that successful methods to synthesize oligosaccharides and glycoconjugates... 

The ability to synthesize chemically short sequences of single-stranded DNA (oligonucleotides) is an essential part of many aspects of genetic engineering. The method most frequently employed is that of solid-phase synthesis, where the basic philosophy is the same as that in solid-phase peptide synthesis (see Section 13.6.3). In other words, the growing nucleic acid is attached to a suitable solid support, protected nucleotides are supplied in the appropriate sequence, and each addition is followed by repeated coupling and deprotection cycles. 

Biomacromolecules and biopolymers have also been put to use as templates for the synthesis of new materials, or models for the study of molecular mechanisms in nature. Exanq>Ies are nucleic acid synthetic alternatives (Eschenmoser 1999), P- and y-peptide synthetic analoguesofnatural a-peptides (Seebach 2001), and analogues ofpoly-(i )-3-hydroxybutanoic acid. The latter can be obtained from chemical synthesis (Seebach 2001) or the culture of engineered Pseudomonas strains (Kessler 2001). 

Innovation and Perspectives in Solid Phase Synthesis Combinatorial Libraries Peptides, Proteins and Nucleic Acids—Small Molecule Organic Chemical Diversity, Collected Papers, International Symposium, 5th, London, Sept. 2-6, 19971999, 201-204. 

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