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Symmetry
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Amino Acid Chirality
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Amino Acid Chirality

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 March 2019) | Viewed by 22408

Special Issue Editor

Dr. Lorenzo Botta

E-Mail Website
Guest Editor
Department of Biological and Ecological Sciences, University of Tuscia, 01100 Viterbo, Italy
Interests: medicinal chemistry; organic syntheisis; prebiotic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

D-isomers of amino acids are uncommon in living organisms; in fact, they are usually called “non-natural” amino acids. Moreover, D-stereoisomers were long considered to have minor functions in biological processes compared to L-ones. On the other hand, evidence has shown that D-amino acids are present in bacterial cell walls, antibiotics, mammals, and in humans and also that they possess specific biological functions.

D-amino acids, having unique stereochemistry properties, present increased resistance towards most endogenous enzymes, and their metabolisms are associated with neurological disorders, such as schizophrenia, ischemia, epilepsy and neurodegeneration.  

This Special Issue intends to cover recent advances in the chemistry and the therapeutic uses of D-amino acids. This includes identification in a prebiotic scenario, the preparation, the incorporation in peptides and peptidomimetics, and their biological evaluations.

Prof. Dr. Lorenzo Botta
Guest Editor

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Symmetry is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2400 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • D amino acids
  • prebiotic chemistry
  • biological activity
  • peptidomimetics

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Published Papers (4 papers)

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Research

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10 pages, 1495 KiB  
Article
Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine
by Haibo Mei, Zizhen Yin, Toshio Miwa, Hiroki Moriwaki, Hidenori Abe, Jianlin Han and Vadim A. Soloshonok
Symmetry 2019, 11(4), 578; https://doi.org/10.3390/sym11040578 - 21 Apr 2019
Cited by 25 | Viewed by 7601
Abstract
In this work we report a convenient asymmetric synthesis of Fmoc-(S)-6,6,6-trifluoro-norleucine via alkylation reaction of chiral glycine equivalent. The target amino acid of 99% enantiomeric purity was prepared with 82.4% total yield (three steps). Full article
(This article belongs to the Special Issue Amino Acid Chirality)
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16 pages, 5825 KiB  
Article
Investigation of the Stereochemical-Dependent DNA and RNA Binding of Arginine-Based Nucleopeptides
by Stefano Tomassi, Francisco Franco Montalban, Rosita Russo, Ettore Novellino, Anna Messere and Salvatore Di Maro
Symmetry 2019, 11(4), 567; https://doi.org/10.3390/sym11040567 - 19 Apr 2019
Cited by 11 | Viewed by 3549
Abstract
Nucleopeptides represent an intriguing class of nucleic acid analogues, in which nucleobases are placed in a peptide structure. The incorporation of D- and/or L-amino acids in nucleopeptide molecules allows the investigation of the role of backbone stereochemistry in determining the formation of DNA [...] Read more.
Nucleopeptides represent an intriguing class of nucleic acid analogues, in which nucleobases are placed in a peptide structure. The incorporation of D- and/or L-amino acids in nucleopeptide molecules allows the investigation of the role of backbone stereochemistry in determining the formation of DNA and RNA hybrids. Circular Dichroism (CD) spectroscopic studies indicated the nucleopeptide as having fully l-backbone configuration-formed stable hybrid complexes with RNA molecules. Molecular Dynamics (MD) simulations suggested a potential structure of the complex resulting from the interaction between the l-nucleopeptide and RNA strand. From this study, both the backbone (ionics and H-bonds) and nucleobases (pairing and π-stacking) of the chiral nucleopeptide appeared to be involved in the hybrid complex formation, highlighting the key role of the backbone stereochemistry in the formation of the nucleopeptide/RNA complexes. Full article
(This article belongs to the Special Issue Amino Acid Chirality)
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Review

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40 pages, 29383 KiB  
Review
α-Amino Acids as Synthons in the Ugi-5-Centers-4-Components Reaction: Chemistry and Applications
by Sveva Pelliccia, Ilenia Antonella Alfano, Ubaldina Galli, Ettore Novellino, Mariateresa Giustiniano and Gian Cesare Tron
Symmetry 2019, 11(6), 798; https://doi.org/10.3390/sym11060798 - 15 Jun 2019
Cited by 8 | Viewed by 5855
Abstract
Since the first reports, the Ugi four-component reaction (U-4CR) has been recognized as a keystone transformation enabling the synthesis of peptide mimetics in a single step and with high atom economy. In recent decades, the U-4CR has been a source of inspiration for [...] Read more.
Since the first reports, the Ugi four-component reaction (U-4CR) has been recognized as a keystone transformation enabling the synthesis of peptide mimetics in a single step and with high atom economy. In recent decades, the U-4CR has been a source of inspiration for many chemists fascinated by the possibility of identifying new efficient organic reactions by simply changing one of the components or by coupling in tandem the multicomponent process with a huge variety of organic transformations. Herein we review the synthetic potentialities, the boundaries, and the applications of the U-4CR involving α-amino acids, where the presence of two functional groups—the amino and the carboxylic acids—allowed a 5-center 4-component Ugi-like reaction, a powerful tool to gain access to drug-like multi-functionalized scaffolds. Full article
(This article belongs to the Special Issue Amino Acid Chirality)
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14 pages, 3083 KiB  
Review
Occurrence of the d-Proline Chemotype in Enzyme Inhibitors
by Elena Lenci and Andrea Trabocchi
Symmetry 2019, 11(4), 558; https://doi.org/10.3390/sym11040558 - 18 Apr 2019
Cited by 9 | Viewed by 4559
Abstract
Natural and nonnatural amino acids represent important building blocks for the development of peptidomimetic scaffolds, especially for targeting proteolytic enzymes and for addressing protein–protein interactions. Among all the different amino acids derivatives, proline is particularly relevant in chemical biology and medicinal chemistry due [...] Read more.
Natural and nonnatural amino acids represent important building blocks for the development of peptidomimetic scaffolds, especially for targeting proteolytic enzymes and for addressing protein–protein interactions. Among all the different amino acids derivatives, proline is particularly relevant in chemical biology and medicinal chemistry due to its secondary structure’s inducing and stabilizing properties. Also, the pyrrolidine ring is a conformationally constrained template that can direct appendages into specific clefts of the enzyme binding site. Thus, many papers have appeared in the literature focusing on the use of proline and its derivatives as scaffolds for medicinal chemistry applications. In this review paper, an insight into the different biological outcomes of d-proline and l-proline in enzyme inhibitors is presented, especially when associated with matrix metalloprotease and metallo-β-lactamase enzymes. Full article
(This article belongs to the Special Issue Amino Acid Chirality)
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