Bioactive Amino Acids, Peptides and Peptidomimetics Containing Silicon

Sieburth, Scott McN.

doi:10.1007/978-94-017-9439-8_8

Cited by 5 publications

(2 citation statements)

References 75 publications

(82 reference statements)

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“…In this context, silicon-containing amino acids are particularly attractive, specifically in view of their incorporation into bioactive compounds, including peptides, to modify their structure and increase their lipophilicity . On the other hand, peptides incorporating a silicon atom in their backbone as a silanediol group have been used as mimics of transition state and have acted as potent protease inhibitors, as reviewed by Sieburth. , Several compounds with silicon-containing amino acids have entered clinical studies or have been developed for applications in agriculture …”

Section: Introductionmentioning

confidence: 99%

“…8 On the other hand, peptides incorporating a silicon atom in their backbone as a silanediol group have been used as mimics of transition state and have acted as potent protease inhibitors, as reviewed by Sieburth. 9,10 Several compounds with silicon-containing amino acids have entered clinical studies or have been developed for applications in agriculture. 11 One of the most efficient enantioselective methods for preparation of α-amino acids is by alkylation of the α-carbon of an enolate derived from a chiral glycine equivalent.…”

Section: Introductionmentioning

confidence: 99%

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Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

et al. 2016

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Unnatural α-amino acids form a family of essential molecules used for, among other applications, the synthesis of modified peptides, to improve resistance to proteolytic enzyme degradation, and to modulate physico- and biochemical properties of bioactive peptides as well as chiral inducers in asymmetric synthesis. Among them, silicon-containing unnatural amino acids are becoming an interesting new class of building blocks. The replacement of carbon atoms in bioactive substances with silicon is becoming increasingly popular. Peptides containing silyl amino acids hold great promise for maintaining or reinforcing the biological activity of active compounds, while they simultaneously enhance their resistance to enzyme degradation. In addition, the lipophilicity of the silicon atom facilitates their membrane crossing and their bioavailability. Nowadays, the interest of the pharmaceutical industry in peptide- and protein-based therapies is increasing. In this respect, silicon-containing amino acids and peptides are likely to be a significant part of future innovations in this area, and more generally in the area of biomolecules. In this process, commercial availability of silicon-containing amino acids is necessary: new syntheses have been developed, and work in this area is ongoing. This review aims to be a comprehensive and general summary of the different methods used to prepare silicon-containing amino acids and their implications on conformational structures and biological applications when they are incorporated into bioactive molecules.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

et al. 2016

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Silanediols, Phosphoramides, and Other OH ‐ and NH ‐Based H‐Donor Catalysts

Leveille

Mattson

2021

Anion‐Binding Catalysis

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Intersecting Xenobiology and Neometabolism To Bring Novel Chemistries to Life

Nieto-Domínguez

Nikel

2020

ChemBioChem

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The diversity of life relies on a handful of chemical elements (carbon, oxygen, hydrogen, nitrogen, sulfur and phosphorus) as part of essential building blocks; some other atoms are needed to a lesser extent, but most of the remaining elements are excluded from biology. This circumstance limits the scope of biochemical reactions in extant metabolism – yet it offers a phenomenal playground for synthetic biology. Xenobiology aims to bring novel bricks to life that could be exploited for (xeno)metabolite synthesis. In particular, the assembly of novel pathways engineered to handle nonbiological elements (neometabolism) will broaden chemical space beyond the reach of natural evolution. In this review, xeno‐elements that could be blended into nature's biosynthetic portfolio are discussed together with their physicochemical properties and tools and strategies to incorporate them into biochemistry. We argue that current bioproduction methods can be revolutionized by bridging xenobiology and neometabolism for the synthesis of new‐to‐nature molecules, such as organohalides.

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Bioactive Amino Acids, Peptides and Peptidomimetics Containing Silicon

Cited by 5 publications

References 75 publications

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

Silanediols, Phosphoramides, and Other OH ‐ and NH ‐Based H‐Donor Catalysts

Intersecting Xenobiology and Neometabolism To Bring Novel Chemistries to Life

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