Approach, to peptide synthesis

Other than the biochemical methods typified by the synthesis of insulin there are two major approaches to peptide synthesis... 

JC Hendrix, JT Jarrett, ST Anisfield, PT Lansbury. Studies related to a convergent fragment-coupling approach to peptide synthesis using the Kaiser oxime resin. J Org Chem 57, 3414, 1992. 

Amino acid residues are added by beginning at the C terminus in the Merrifield solid-phase approach to peptide synthesis. Thus the synthesis of Phe-Gly requires glycine to be anchored to the solid support. Begin by protecting glycine as its tert-butoxycarbonyl (Boc) derivative. 

Jre you understand the approach to peptide synthesis explained in the chapter. 

Mukaiyama reaction, a redox condensation approach to peptide synthesis. A disulfide (2,2 -dipyridyldisulfide) reduction combined with a phosphine (triphenylphos-phine) oxidation provides the driving force for the condensation of the carboxy component with the amino component [T. Mukaiyama et al., in The Peptides Analysis, Synthesis, Biolc, Volume 2, E. Gross,... 

In 1962, a new approach to peptide synthesis was introduced by R. B. Mer-rifield. The key idea was that the first amino acid residue would be attached to an insoluble polymer. In practice, the attachment was accomplished by introducing chloromethyl groups on polystyrene and alkylating the carboxyl end of the first residue ... 

A novel approach to peptide synthesis has been the use of a chloromethylated polystyrene polymer as an insoluble but porous solid phase on which the coupling reactions are carried out. Attachment to the polymer, constitutes protection of the carboxyl group (as a modified benzyl ester), and the peptide is lengthened from its amino-end by successive carbodiimide couplings. The method has been applied to the synthesis of a tetrapeptide, but incomplete reactions lead to the accumulation of by products. Further development of this interesting method is awaited. 

Confusion in the literature regarding the sensory character of the BMP and a new approach to peptide synthesis permitting larger scale synthesis, prompted van Wassenaar et al. [56] to do more a thorough sensory evaluation. They found that the BMP they synthesized and an equivalent commercial product lacked any taste. 

Eattori, D., O. Kinzel, P. Ingallinella, E. Bianchi, and A. Pessi. A practical approach to the synthesis of hairpin polyamide-peptide conjugates through the use of a safety-catch linker. Bioorg. Med. Chem. Lett. 2002, 12, 1143-1147. 

Lloyd-Williams P, Albericio F, Giralt E (1997) Chemical approaches to the synthesis of peptides and proteins. CRC, Boca Raton... 

Combinatorial approaches to the synthesis of libraries of peptides, nucleotides, and many classes of small organic molecules are well documented.35 However, the field of oligosaccharide combinatorial chemistry is still in its infancy.36 The slow development is due to the inherent complexities in the synthesis of oligosaccharides. 

Lloyd-Williams, R, Albericio, F. and Giralt, E. (1997) Chemical Approaches to the Synthesis of Peptides and Proteins. 367pp. CRC Press. The main focus is on large molecules, with 1343 references. 

Chemoselective ligation of peptides using the free amino terminal as nucleophile and a thiobenzyl thioester C-terminal amino acid as electrophile provides an efficient approach to the synthesis of proteins with several hundred residues [30]. From this perspective the introduction of non-natural amino acids into proteins becomes a possibility rather than a problem and chemoselective ligation is thus a prospect for the future for the incorporation of new functionality. 

The standard approach to the synthesis of peptides containing disulfide bridges is to use S-protected cysteine derivatives for chain elongation and then subsequently form the disulfide by oxidation of the final S-protected or S-unprotected cysteine peptides (Section 6.1.1). The alternative approach, based on the use of suitably protected symmetrical or unsymmetrical cystine derivatives for the synthesis of disulfide bridged homo-, or heterodimers, besides exhibiting the difficulties discussed in Section 6.1.3, was recently found to generate under... 

Phenylglycine derivatives are key intermediates in the synthesis of vancomycin. 81-85 This amino add is also very useful for incorporation into oxazolidinones as a chiral aux-iliaryt45,47 48 53 86 87 and for modulating bioactivities of peptides and peptidomimeticsJ85,88 There are several possible approaches to the synthesis of phenylglycines, including the Strecker reaction and the Evans electrophilic azidation reaction.181 ... 

Solid-phase peptide synthesis has become widely used for the preparation of peptides built from a-amino acids of varying sizes and complexity, and also in the recent synthetic approaches to peptide libraries. It has been recognized that the use of solid-phase protocols for the synthesis of (3-peptides is likely to make them more attractive lead compounds in drug discovery. Although still at an early stage, work has begun to develop suitable protocols for automated (3-peptide synthesis. 

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