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Journal articles on the topic 'Unnatural amino acids'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Magliery, Thomas. "Unnatural Protein Engineering: Producing Proteins with Unnatural Amino Acids." Medicinal Chemistry Reviews - Online 2, no. 4 (2005): 303–23. http://dx.doi.org/10.2174/1567203054637542.

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2

Archer, I., I. Fotheringham, R. Carr, R. Speight, and N. J. Turner. "Preparative deracemization of unnatural amino acids." Biochemical Society Transactions 34, no. 2 (2006): 287. http://dx.doi.org/10.1042/bst20060287.

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3

Hausmann, Corinne D., Jiqiang Ling, and Michael Ibba. "The unnatural culture of amino acids." Nature Methods 4, no. 3 (2007): 205–6. http://dx.doi.org/10.1038/nmeth0307-205.

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4

Fotheringham, I., I. Archer, R. Carr, R. Speight, and N. J. Turner. "Preparative deracemization of unnatural amino acids." Biochemical Society Transactions 34, no. 2 (2006): 287–90. http://dx.doi.org/10.1042/bst0340287.

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Unnatural amino acids are a growing class of intermediates required for pharmaceuticals, agrochemicals and other industrial products. However, no single method has proven sufficiently versatile to prepare these compounds broadly at scale. To address this need, we have developed a general chemoenzymatic process to prepare enantiomerically pure L- and D-amino acids in high yield by deracemization of racemic starting materials. This method involves the concerted action of an enantioselective oxidase biocatalyst and a non-selective chemical reducing agent to effect the stereoinversion of one enant

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5

Kigawa, Takanori, Shigeyuki Yokoyama, and Tatsuo Miyazawa. "Incorporation of unnatural amino acids proteins." Kobunshi 39, no. 7 (1990): 500–503. http://dx.doi.org/10.1295/kobunshi.39.500.

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6

Bilgiçer, Basar, and Krishna Kumar. "Protein Design Using Unnatural Amino Acids." Journal of Chemical Education 80, no. 11 (2003): 1275. http://dx.doi.org/10.1021/ed080p1275.

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7

Hallam, Trevor J., Erik Wold, Alan Wahl, and Vaughn V. Smider. "Antibody Conjugates with Unnatural Amino Acids." Molecular Pharmaceutics 12, no. 6 (2015): 1848–62. http://dx.doi.org/10.1021/acs.molpharmaceut.5b00082.

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8

Zhang, William H., Gottfried Otting, and Colin J. Jackson. "Protein engineering with unnatural amino acids." Current Opinion in Structural Biology 23, no. 4 (2013): 581–87. http://dx.doi.org/10.1016/j.sbi.2013.06.009.

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9

Nödling, Alexander R., Luke A. Spear, Thomas L. Williams, Louis Y. P. Luk, and Yu-Hsuan Tsai. "Using genetically incorporated unnatural amino acids to control protein functions in mammalian cells." Essays in Biochemistry 63, no. 2 (2019): 237–66. http://dx.doi.org/10.1042/ebc20180042.

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Abstract Genetic code expansion allows unnatural (non-canonical) amino acid incorporation into proteins of interest by repurposing the cellular translation machinery. The development of this technique has enabled site-specific incorporation of many structurally and chemically diverse amino acids, facilitating a plethora of applications, including protein imaging, engineering, mechanistic and structural investigations, and functional regulation. Particularly, genetic code expansion provides great tools to study mammalian proteins, of which dysregulations often have important implications in hea

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10

Adhikari, Anup, Bibek Raj Bhattarai, Ashika Aryal, et al. "Reprogramming natural proteins using unnatural amino acids." RSC Advances 11, no. 60 (2021): 38126–45. http://dx.doi.org/10.1039/d1ra07028b.

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11

Hallam, Trevor J., and Vaughn V. Smider. "Unnatural amino acids in novel antibody conjugates." Future Medicinal Chemistry 6, no. 11 (2014): 1309–24. http://dx.doi.org/10.4155/fmc.14.79.

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12

Liu, Chang C., Lei Qi, Charles Yanofsky, and Adam P. Arkin. "Regulation of transcription by unnatural amino acids." Nature Biotechnology 29, no. 2 (2011): 164–68. http://dx.doi.org/10.1038/nbt.1741.

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13

Mendel, D., J. Ellman, Z. Chang, D. Veenstra, P. Kollman, and P. Schultz. "Probing protein stability with unnatural amino acids." Science 256, no. 5065 (1992): 1798–802. http://dx.doi.org/10.1126/science.1615324.

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14

Pojitkov, Alexander E., Elena N. Efremenko, and Sergej D. Varfolomeev. "Unnatural amino acids in enzymes and proteins." Journal of Molecular Catalysis B: Enzymatic 10, no. 1-3 (2000): 47–55. http://dx.doi.org/10.1016/s1381-1177(00)00107-7.

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15

Micklitsch, Christopher M., Qian Yu та Joel P. Schneider. "Unnatural multidentate metal ligating α-amino acids". Tetrahedron Letters 47, № 35 (2006): 6277–80. http://dx.doi.org/10.1016/j.tetlet.2006.06.128.

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16

Young, Douglas D., Jessica Torres-Kolbus, and Alexander Deiters. "Microwave-assisted synthesis of unnatural amino acids." Bioorganic & Medicinal Chemistry Letters 18, no. 20 (2008): 5478–80. http://dx.doi.org/10.1016/j.bmcl.2008.09.025.

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17

Anthony-Cahill, Spencer J., Michael C. Griffith, Christopher J. Noren, Daniel J. Suich, and Peter G. Schultz. "Site-specific mutagenesis with unnatural amino acids." Trends in Biochemical Sciences 14, no. 10 (1989): 400–403. http://dx.doi.org/10.1016/0968-0004(89)90287-9.

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18

Chung, Hyunho, and Peter G. Schultz. "Probing Ras function with unnatural amino acids." Chemistry & Biology 1 (April 1994): vi—vii. http://dx.doi.org/10.1016/1074-5521(94)90020-5.

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19

Ko, Wooseok, Sanggil Kim, Kyubong Jo, and Hyun Soo Lee. "Genetic incorporation of recycled unnatural amino acids." Amino Acids 48, no. 2 (2015): 357–63. http://dx.doi.org/10.1007/s00726-015-2087-x.

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20

ACOSTA, C. K., M. L. BAHR, J. E. JUN BURDETT, et al. "ChemInform Abstract: Synthesis of Unnatural Amino Acids." ChemInform 22, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199133264.

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21

Cheruku, Pradeep, Jen-Huang Huang, Hung-Ju Yen, et al. "Tyrosine-derived stimuli responsive, fluorescent amino acids." Chemical Science 6, no. 2 (2015): 1150–58. http://dx.doi.org/10.1039/c4sc02753a.

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22

Gao, Wei, Ning Bu, and Yuan Lu. "Efficient Incorporation of Unnatural Amino Acids into Proteins with a Robust Cell-Free System." Methods and Protocols 2, no. 1 (2019): 16. http://dx.doi.org/10.3390/mps2010016.

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Unnatural proteins are crucial biomacromolecules and have been widely applied in fundamental science, novel biopolymer materials, enzymes, and therapeutics. Cell-free protein synthesis (CFPS) system can serve as a robust platform to synthesize unnatural proteins by highly effective site-specific incorporation of unnatural amino acids (UNAAs), without the limitations of cell membrane permeability and the toxicity of unnatural components. Here, we describe a quick and simple method to synthesize unnatural proteins in CFPS system based on Escherichia coli crude extract, with unnatural orthogonal

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23

Katti, Kalpana S., Avinash H. Ambre, Nicholas Peterka, and Dinesh R. Katti. "Use of unnatural amino acids for design of novel organomodified clays as components of nanocomposite biomaterials." Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences 368, no. 1917 (2010): 1963–80. http://dx.doi.org/10.1098/rsta.2010.0008.

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Sodium montmorillonite (Na-MMT) clay was modified with three different unnatural amino acids in order to design intercalated clay structures that may be used for bone biomaterials applications. Prior work on polymer–clay nanocomposites (PCNs) has indicated the effect of the appropriate choice of modifiers on enhancing properties of PCNs. Our X-ray diffraction results indicate an increase in the d -spacing of Na-MMT clay after it was modified with the three unnatural amino acids. Transmission Fourier transform infrared spectroscopy experiments were carried out on the unmodified and modified MMT

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24

Zhang, F., Q. Sheikh, B. Chen, K. Tee та T. Wong. "Expanding the enzymatic toolbox for β-amino acids and unnatural amino acids manufacturing". New Biotechnology 85 (березень 2025): 181. https://doi.org/10.1016/j.nbt.2024.08.257.

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25

Bąchor, Urszula, Agnieszka Lizak, Remigiusz Bąchor та Marcin Mączyński. "5-Amino-3-methyl-Isoxazole-4-carboxylic Acid as a Novel Unnatural Amino Acid in the Solid Phase Synthesis of α/β-Mixed Peptides". Molecules 27, № 17 (2022): 5612. http://dx.doi.org/10.3390/molecules27175612.

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The hybrid peptides consisting of α and β-amino acids show great promise as peptidomimetics that can be used as therapeutic agents. Therefore, the development of new unnatural amino acids and the methods of their incorporation into the peptide chain is an important task. Here, we described our investigation of the possibility of 5-amino-3-methyl-isoxazole-4-carboxylic acid (AMIA) application in the solid phase peptide synthesis. This new unnatural β-amino acid, presenting various biological activities, was successfully coupled to a resin-bound peptide using different reaction conditions, inclu

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26

Liu, Chang C., Antha V. Mack, Meng-Lin Tsao, et al. "Protein evolution with an expanded genetic code." Proceedings of the National Academy of Sciences 105, no. 46 (2008): 17688–93. http://dx.doi.org/10.1073/pnas.0809543105.

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We have devised a phage display system in which an expanded genetic code is available for directed evolution. This system allows selection to yield proteins containing unnatural amino acids should such sequences functionally outperform ones containing only the 20 canonical amino acids. We have optimized this system for use with several unnatural amino acids and provide a demonstration of its utility through the selection of anti-gp120 antibodies. One such phage-displayed antibody, selected from a naïve germline scFv antibody library in which six residues in VH CDR3 were randomized, contains su

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27

S.Makhathini, Sifiso, Sukant K. Das, Thishana Singh, et al. "Stereoselective synthesis towards unnatural proline based amino acids." Arkivoc 2016, no. 3 (2016): 134–44. http://dx.doi.org/10.3998/ark.5550190.p009.462.

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28

Voloshchuk, Natalya, and Jin Kim Montclare. "Incorporation of unnatural amino acids for synthetic biology." Mol. BioSyst. 6, no. 1 (2010): 65–80. http://dx.doi.org/10.1039/b909200p.

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29

Tian, Feng, Meng-Lin Tsao, and Peter G. Schultz. "A Phage Display System with Unnatural Amino Acids." Journal of the American Chemical Society 126, no. 49 (2004): 15962–63. http://dx.doi.org/10.1021/ja045673m.

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30

Bednar, Rodney A., Catherine McCaffrey, and Kaiyu Shan. "Introduction of unnatural amino acids into chalcone isomerase." Bioconjugate Chemistry 2, no. 4 (1991): 211–16. http://dx.doi.org/10.1021/bc00010a004.

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31

Liao, J. "Protein and Cellular Engineering with Unnatural Amino Acids." Biotechnology Progress 23, no. 1 (2007): 28–31. http://dx.doi.org/10.1021/bp060369d.

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32

Raliski, Benjamin K., Christina A. Howard, and Douglas D. Young. "Site-Specific Protein Immobilization Using Unnatural Amino Acids." Bioconjugate Chemistry 25, no. 11 (2014): 1916–20. http://dx.doi.org/10.1021/bc500443h.

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33

Kim, Chan Hyuk, Jun Y. Axup, and Peter G. Schultz. "Protein conjugation with genetically encoded unnatural amino acids." Current Opinion in Chemical Biology 17, no. 3 (2013): 412–19. http://dx.doi.org/10.1016/j.cbpa.2013.04.017.

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34

Hartman, M. C. T., K. Josephson, and J. W. Szostak. "Enzymatic aminoacylation of tRNA with unnatural amino acids." Proceedings of the National Academy of Sciences 103, no. 12 (2006): 4356–61. http://dx.doi.org/10.1073/pnas.0509219103.

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35

Bolm, Carsten, Ingo Schiffers, Christian L. Dinter, Laurent Defrère, Arne Gerlach та Gerhard Raabe. "Efficient Asymmetric Synthesis of Unnatural β-Amino Acids". Synthesis 2001, № 11 (2001): 1719–30. http://dx.doi.org/10.1055/s-2001-16745.

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36

Fernandez, M. M., A. O. Margot, C. A. Falender, H. W. Blanch, and D. S. Clark. "Enzymatic synthesis of peptides containing unnatural amino acids." Enzyme and Microbial Technology 17, no. 11 (1995): 964–71. http://dx.doi.org/10.1016/0141-0229(94)00119-7.

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37

Agostini, Federica, Jan‐Stefan Völler, Beate Koksch, Carlos G. Acevedo‐Rocha, Vladimir Kubyshkin, and Nediljko Budisa. "Biocatalysis with Unnatural Amino Acids: Enzymology Meets Xenobiology." Angewandte Chemie International Edition 56, no. 33 (2017): 9680–703. http://dx.doi.org/10.1002/anie.201610129.

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38

Maluch, Izabela, Justyna Czarna, and Marcin Drag. "Applications of Unnatural Amino Acids in Protease Probes." Chemistry – An Asian Journal 14, no. 23 (2019): 4103–13. http://dx.doi.org/10.1002/asia.201901152.

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39

Brittain, William D. G., Carissa M. Lloyd, and Steven L. Cobb. "Synthesis of complex unnatural fluorine-containing amino acids." Journal of Fluorine Chemistry 239 (November 2020): 109630. http://dx.doi.org/10.1016/j.jfluchem.2020.109630.

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40

Aycock, R. A., D. B. Vogt, and N. T. Jui. "A practical and scalable system for heteroaryl amino acid synthesis." Chemical Science 8, no. 12 (2017): 7998–8003. http://dx.doi.org/10.1039/c7sc03612d.

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41

Baglai, Iaroslav, Michel Leeman, Klaus Wurst, Bernard Kaptein, Richard M. Kellogg, and Willem L. Noorduin. "The Strecker reaction coupled to Viedma ripening: a simple route to highly hindered enantiomerically pure amino acids." Chemical Communications 54, no. 77 (2018): 10832–34. http://dx.doi.org/10.1039/c8cc06658b.

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We introduce a methodology based on a combination of the classical Strecker reaction, simple condensation and Viedma ripening, which allows absolute asymmetric synthesis of highly sterically hindered α-amino acids. As proof-of-principle, enantiomerically pure unnatural α-amino acids tert-leucine and α-(1-adamantyl)glycine have been obtained.

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42

Drienovská, Ivana, Ana Rioz-Martínez, Apparao Draksharapu, and Gerard Roelfes. "Novel artificial metalloenzymes by in vivo incorporation of metal-binding unnatural amino acids." Chemical Science 6, no. 1 (2015): 770–76. http://dx.doi.org/10.1039/c4sc01525h.

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43

Janczewski, Łukasz, Dorota Kręgiel, and Beata Kolesińska. "Synthesis of Isothiocyanates Using DMT/NMM/TsO− as a New Desulfurization Reagent." Molecules 26, no. 9 (2021): 2740. http://dx.doi.org/10.3390/molecules26092740.

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Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO−) as a desulfurization reagent. For the synthesis of aliphatic

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44

Magrioti, Victoria, Georgia Antonopoulou, Evlambia Pantoleon, and George Kokotos. "Synthesis of 2-amino alcohols and unnatural amino acids from serine." Arkivoc 2002, no. 13 (2003): 55–61. http://dx.doi.org/10.3998/ark.5550190.0003.d07.

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45

Caligiuri, Antonio, Paola D'Arrigo, Elena Rosini, et al. "Enzymatic Conversion of Unnatural Amino Acids by YeastD-Amino Acid Oxidase." Advanced Synthesis & Catalysis 348, no. 15 (2006): 2183–90. http://dx.doi.org/10.1002/adsc.200606188.

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46

Abdelkader, E. H., A. Feintuch, X. Yao, et al. "Protein conformation by EPR spectroscopy using gadolinium tags clicked to genetically encoded p-azido-l-phenylalanine." Chemical Communications 51, no. 88 (2015): 15898–901. http://dx.doi.org/10.1039/c5cc07121f.

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47

Iannuzzelli, Jacob A., and Rudi Fasan. "Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells." Chemical Science 11, no. 24 (2020): 6202–8. http://dx.doi.org/10.1039/d0sc01699c.

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48

Elazar, Meyer. "Preparation of Intermediates for Organic Synthsis." Technium BioChemMed 6 (December 19, 2023): 73–91. http://dx.doi.org/10.47577/biochemmed.v6i.10421.

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Several synthetic methods are described for the preparation of compounds such as derivatives of natural amino acids, unnatural amino acids, amino esters, oxime esters and amino amides that may serve as intermediates in the synthesis of active pharmaceutical ingredients (APIs) or drugs. The compounds described herein are produced in high yield and purity and the synthetic procedures are detailed along with the NMR spectra of the compounds and useful chemical data relating to these compounds.

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49

Umerani, M. J., H. Yang, P. Pratakshya, J. S. Nowick, and A. A. Gorodetsky. "An aza-Diels–Alder route to quinoline-based unnatural amino acids and polypeptide surrogates." RSC Advances 11, no. 23 (2021): 14132–39. http://dx.doi.org/10.1039/d0ra04783j.

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50

Nishino, Soshi, Masahiro Miura та Koji Hirano. "An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids". Chemical Science 12, № 34 (2021): 11525–37. http://dx.doi.org/10.1039/d1sc03692k.

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