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At the Crossroads of Heterocyclic and Peptide Chemistries. The Aminoacyl Incorporation Reaction in the Synthesis of Medium-Sized Ring Heterocycles (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

The aminoacyl incorporation reaction of peptides is considered in the context of synthetic heterocyclic chemistry with particular emphasis on the scope, mechanism, and major by-products of the reaction. Medium-sized mono- and bicyclic molecules available via aminoacyl incorporation reaction are unique building blocks with significant promise in biomolecular design.

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Notes

  1. The diversity is even higher considering the chiral nature of amino acids: up to four isomers could potentially be prepared for each structure.

  2. The cyclol hypothesis postulating a global 3D network of fused orthoamide units as a general pattern of polypeptide (protein) structure was introduced and advocated by mathematician Dorothy Wrinch until the early 1960s [22, 23] in spite of the lack of a solid physicochemical basis and any experimental evidence. Her weird concept has only some historical value at best and was never considered seriously by contemporaries. Although in certain particular cases the cyclol intermediacy make sense and offer mechanistic explanation to such existing process like maturation of GFP fluorophore [24].

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Authors and Affiliations

  1. Branch of M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 6 Science Ave., Pushchino, 142290, Russia

    V. N. Azev, A. N. Chulin & I. L. Rodionov

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  1. V. N. Azev
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  2. A. N. Chulin
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  3. I. L. Rodionov
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Correspondence to V. N. Azev.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 166-181, February, 2014.

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Azev, V.N., Chulin, A.N. & Rodionov, I.L. At the Crossroads of Heterocyclic and Peptide Chemistries. The Aminoacyl Incorporation Reaction in the Synthesis of Medium-Sized Ring Heterocycles (Review). Chem Heterocycl Comp 50, 145–159 (2014). https://doi.org/10.1007/s10593-014-1457-8

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