Peptide segment coupling

LA Carpino, D Ionescu, A El-Faham. Peptide segment coupling in the presence of highly hindered tertiary amines. J Org Chem 61, 2460, 1996. 

P Wang, R Layfield, RJ Mayer, R Ramage. Transfer active ester condensation a novel technique for peptide segment coupling. Tetrahedron Lett 39, 8711, 1998. 

J Blake. Peptide segment coupling in aqueous medium silver ion activation of the thiolcarboxylic group. Int J Pept Prot Res 17, 273, 1981. 

DM Coltart. Peptide segment coupling by prior ligation and proximity-induced intramolecular acyl transfer. Tetrahedron 56, 3449-3491, 2000. 

L.A. Carpino, A. El-Faham, Effect of Tertiary Bases on 0-Benzotriazolyluronium Salt-Induced Peptide Segment Coupling, J. Org. Chem. 59 695- 698, 1994. 

T. Nakatsuka, T. Sasaki, E.T. Kaiser, Peptide segment coupling catalyzed by the semisynthetic enzyme thiolsubtilisin, J. Am. Chem. Soc. 1987, 109, 3808. 

About 50 aldehydes 3 have been tested as the carbonyl components of peptide segment coupling (SC) according to Scheme 1,11 (ref. 1), but no satisfactory results have been obtained. 

Synthetic haptens mimicking some critical epitopic structures on larger macromolecules are often conjugated to carriers to create an immune response to the larger parent molecule. For instance, short peptide segments can be synthesized from the known sequence of a viral coat protein and coupled to a carrier to induce immunogenicity toward the native virus. This type of synthetic approach to immunogen production has become the basis of much of the current research into the creation of vaccines. 

S Pass, B Amit, A Parchomik. Racemization-free photochemical coupling of peptide segments. (Fmoc-amino-acid chlorides) J Am Chem Soc 103, 7674, 1981. 

JC Califano, C Devin, J Shao, JK Blodgett, RA Maki, KW Funk, JC Tolle. Copper(II)-containing racemization suppressors and their use in segment coupling reactions, in J Martinez, J-A Fehrentz, eds. Peptides 2000. Proceedings of the 26th European Peptide Symposium, EDK, Paris, 2001, pp 99-100. 

There have been reports that urethane was produced when the mixed-anhydride method was employed for the coupling of segments. However, studies on urethane formation during the aminolysis of mixed anhydrides of peptides have never been carried out. The anhydrides are too unstable to be isolated. The activated moiety of the peptide cyclizes too quickly to the 2,4-dialkyl-5(4//)-oxazolonc (see Section 2.23), and since the time allowed to generate the anhydride in segment couplings is always limited to avoid epimerization, one cannot exclude the possibility that the urethane that was produced originated by aminolysis of unconsumed chloroformate. 

Scheme 17 Silver Ion Activated Coupling between a Thiocarboxy Group and the a-Amine of Another Peptide Segment 981...

Scheme 7 Coupling of Peptide Segments on a Cyclodextrin Derivative 251...

Scheme 21 Coupling of Peptide Segments to a Bipyridyl Ligand and Fe2+ Induced Self-Assembly of a Three-Helix Supramolecular Structure 56-57 ...

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