Oligopeptide, definition

Short chains of amino acid residues are known as di-, tri-, tetrapeptide, and so on, but as the number of residues increases the general names oligopeptide and polypeptide are used. When the number of chains grow to hundreds, the name protein is used. There is no definite point at which the name polypeptide is dropped for protein. Twenty common amino acids appear regularly in peptides and proteins of all species. Each has a distinctive side chain (R in Figure 45.3) varying in size, charge, and chemical reactivity. 

In the following I will present a model to tackle this question. We are at the level of speculations, but we will use some known facts. For example, let s start from the condensation of NCA-anhydrides, a reaction which, as we have seen in the previous chapter, is considered prebiotic. In this way, oligopeptides up to (say) a length of ten can be built, possibly under thermodynamic control, but starting from a definite set of conditions (amino-acid composition in the starting mixture, pH, salinity, etc.). We can assume, and this is actually quite reasonable, that in this way copious libraries of different decapeptides have been formed, each in a significant concentration. 

In recent years, there has been increasing awareness regarding the importance of transporters in the absorption and disposition of NMEs. While the major portion of NMEs or marketed drugs traverse cell membranes by passive diffusion, there are numerous examples where the involvement of specialized transport mechanisms has been demonstrated. Examples include the role of oligopeptide transporters in the intestinal absorption of P-lactam antibiotics, angiotensinconverting enzyme (ACE) inhibitors, and novel NMEs as well as the role of P-glycoprotein (P-gp) in the secretion of molecules into the intestine [11,77—79]. Transfection of cells with the transporter protein of interest has permitted the evaluation of precise cellular mechanisms of uptake and transport of NMEs. Transfected cell lines by definition are tailor-made to overexpress the protein of... 

Tsogoeva and coworkers reported the use of oligopeptides of 4-tram-aminopro-hne (tetra- and dipeptides 3 and 4, respectively) as organic catalysts for the Michael reaction of nitroalkanes to cyclic enones. The reaction, in the presence of the achiral additive trans-2,5-dimethylpiperazine, afforded the conjugate addition product in excellent yield and ee up to 88% (Scheme 5.2) [14]. Other dipeptides, with a primary amine at the N-terminus and containing a histidine derivative, were definitely less selective [15] (under the same reaction conditions), while L-proline alone afforded the same product in 93% ee [16]. 

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