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Amino acids selection

Amino acids are the building blocks which are widespread in the Nature. Even of the limited number of the genetically-coded α-amino acids the Nature composes practically unlimited number of proteins. The “success” of proteins in sustaining life and regulating biochemical processes prompted chemists over the world to mimic their structure and function in search for new drug candidates – peptidomimetics1. It is therefore not surprising that the selection of the natural proteinogenic amino acids was substantially enriched by creating new, unnatural amino acids, specially designed to improve pharmacokinetic and pharmacodynamic properties of the peptidomimetics and other biologically active compounds based on them.

At present, many suppliers of the building blocks for drug design offer large selection of the unnatural amino acids. Enamine committed itself to create a library of the unusual amino acids which would differ from the available on the market. First, we offer a number of racemic α-amino acids at the very reasonable prices. The price category, together with extremely wide chemical diversity, makes these amino acids especially attractive in lead discovery by HTS. Examples illustrating chemical diversity of this set can be found below:

EN400-14661 EN400-14693 EN400-14724
EN400-14740 EN400-14791 EN400-14837

Other principles were used when compiling a set of conformationally restricted amino acids. The peptidomimetics obtained on the basis of conformationally restricted unnatural amino acids are expected to be biologically active due to their better preorganization resulting in stronger interaction with target biomolecules2,3. These amino acids are optically pure (where applicable), and often can be supplied in both enantiomeric forms. N-protected derivatives, ready for the automated peptide synthesis are also available. Large selection of cyclic and polycyclic amino acids alows for variation of the geometry of the peptidomimetics in a vide range, fine-tuning the structure to the need of structure-based drug design. Low molecular mass and favourable lipophilicity make them useful in the fragment-based lead discovery. Some examples are shown below:

EN400-08701EN400-15166 EN400-12633
EN400-13332EN400-08700 EN400-13909

Yet another subset of the Enamine Amino Acid Selection Database consists of conformationally restricted β-, γ- and ω- amino acids. Their use in the peptidomimetic design has been shown to lead to extremely unusual structural consequences and promising biological activity, see, for example4 , and references therein. Here, too, chiral compounds are available as single enantiomers of high optical purity. In most cases, these amino acids are available in protected form ready for peptide synthesis.

Representative examples:

EN400-14003 EN400-13912EN400-15210
EN400-15171 EN400-15190 EN400-15201

Finally, Enamine offers a vide variety of the fluorine-substituted α- and γ- amino acids. These compounds can be used in drug design and also as biomarkers, 19F labels in NMR-spectroscopy 5. In the synthesis of the fluorine-substituted amino acids our chemists use the experience in the fluorine chemistry acquired in cutting-edge research carried out at the Ukrainian scientific institutions. Examples:

EN400-12625EN400-13442EN400-15208
EN400-15207 EN400-15205 EN400-08702

 

The complete updated database of the Enamines’ Amino Acid Selection with listed amounts and prices is available here. The compounds are ether in stock or can be prepared in agreed amounts in 2-3 weeks.

1 J. Gante. Angew. Chem. Int. Ed. , 1994, Vol. 33, P. 1699-1720.

2 Igor V. Komarov, Oleksandr O. Grygorenko, Dmytro S. Radchenko, Oleksiy S. Artamonov, Alexander N. Kostyuk, Andrey A. Tolmachev. Libraries of conformationally restricted and rigid amino acids. Chimica Oggi/Chemistry Today, 2006, vol. 24, No 4, p. 22-23

3 Igor V. Komarov, Aleksandr O. Grigorenko, Aleksandr V. Turov, Vladimir P. Khilya. Conformationally rigid cyclic a-amino acids in the design of peptidomimetics, peptide models and biologically active compounds. Russian Chemical Reviews, 2004, vol. 73, No 8, p. 785-810

4 S. Urman, K. Gaus, Y. Yang, U. Strijowski, N. Sewald, S. De Pol, O. Reiser. The constrained amino acid β-ACC confers potency and selectivity to integrin ligands. Angew. Chem. Int. Ed. Engl., 2007, 46, 3976-3978.

5 Pavel K. Mikhailiuk, Sergii Afonin, Alexander N. Chernega, Eduard B. Rusanov, Maxim O. Platonov, Galina G. Dubinina, Marina Berditsch, Anne S. Ulrich, Igor V. Komarov. Conformationally rigid trifluoromethyl-substituted α-amino acid designed for peptide structure analysis by solid-state 19F NMR spectroscopy. Angew.Chem., Int. Ed. Engl., 2006, vol. 45, p. 5659-5661



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