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2-(2-(Tert-Butoxycarbonyl) Propanamido) Acetic Acid ‘NCA-AG’ Synthesis, Characterization and Reaction Optimization for the Preparation

Received: 6 October 2015     Accepted: 23 October 2015     Published: 10 November 2015
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Abstract

2-(2-(tert-butoxycarbonyl) propanamido) acetic acid (NCA-AG) was for the first time prepared using a variation of the Leuchs method. All compounds were characterized using melting point, nuclear magnetic resonance (NMR), ultra violet spectroscopy (UV), Fourier transform infrared spectroscopy (FTIR) and electron spray mass spectroscopy (ESMS). The reaction was optimised to obtain the highest yield by varying the reaction conditions namely; solvent, lewis acid and temperature.

Published in Advances in Biochemistry (Volume 3, Issue 6)
DOI 10.11648/j.ab.20150306.12
Page(s) 72-76
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2015. Published by Science Publishing Group

Keywords

2-(2-(Tert-Butoxycarbonyl) Propanamido) Acetic Acid (NCA-AG), Stereospecific Peptides, Synthetic Silk Substrates, N-Tert-Butoxy Carbonanhydride (NCA)

References
[1] Stainslaw, P. (2000) Models of Biopolymers by Ring Opening Polymerization, Ch 1, CRC Pr ILIc, Berlin, NY.
[2] Deming, T. J., (2000), “Living polymerization of α-amino acid-N-carboxyanhydrides.” J. of Polym. Sci. Part A, 38, 3011-3018.
[3] Deming, T. (2000), “Chain initiation effeciency in cobalt and Nickel mediated polypeptide synthesis“ J. Am. Soc., 122, 5710-5717.
[4] Zhang, S., Anderson, M. A., Ao, Y., Khakh, B. S., Fan, J., Deming , T. J., Sofroniew, M. V., (2013), “Tunable diblock copolypeptide hydrogel depots for local delivery of hydrophobic molecules in healthy and injured central nervous system,” Biomats., 35, 6, 1989–2000.
[5] Jiang, Z. K., Koh, S. B. S, Sato, M., Atanasov, I. C., Johnson, M., Zhou, H, Z. and Deming, T. J. and Wu, L. (2013), “Engineering polypeptide coatings to augment gene transduction and in vivo stability of adenoviruses,” J. Control. Releas., 166, 1, 75–85.
[6] Song, B., Song, J., Zhang, S., Anderson, M. A., Ao, Y., Yang, C. Y., Deming, T. J., Sofroniew, M. V., (2012), “Sustained local delivery of bioactive nerve growth factor in the central nervous system via tunable diblock copolypeptide hydrogel depots” Biomats. 33, 35, 9105-9116.
[7] Tanimoto, S. Yagi, N. and Yamaoka, H., (2009), “Application of Thermosensitive Peptide Copolymer Gels to Removal of Endocrine Disruptor,” Research Letts in Mat. Sci., 2009, 1155.
[8] Jap. Pat. 6.901.974 (1969) to Asahi Chem. Ind.; invs. Wakasa, R., hibata, K., Takahashi, Y., Ishida, S.: CA 71, 13, 373-374.
[9] Levy, A. L. (1950), ‘Anhydro-N-Carboxy-DL-β-Phenylalanine,’ Nature, 165, 4187, 152-152.
[10] Iwakura, Y., Uno, K. and Kang, S. (1965), “Trisphosgene, a crystalline phosgene substitute,” J. polym. Sci (part A-1),” polym. chem., 30, 4, 2867-2879.
[11] Kricheldorf, H. R. (1966) Chem. Ber., 87, 104, 3168-3175.
[12] Cheng, J., Ziller, J. W. and Deming, T., (2000) “Synthesis and Conformational Analysis of Optically Active Poly(ß-peptides)”J. Org. Lett., 2, 13, 143-146.
[13] Leuchs, H. & Geiger, W. (1908), “Über die Anhydride von α-Amino-N-carbonsäuren und die von α-Aminosäuren,” Dtsch.Chem, Ges., 41,1721-1726.
[14] Salamula, E. J., Bredenkamp, M., Bezuidenhout, D. and Nadiye. M. S., (2015), Optimizing of “N - tert - butoxycarbon anhydrides polymerization of NCAs’ AG, SIK and VAV”, Int. Appl. Chem., 11, 4, 409-426.
[15] Wagner S., and Prentice B., Hall Englewood Cliffs, [Online] NJ07632, www.scribd.com/doc/7365634/Superstrong-Material-BioSteel pp 18-25.
[16] Klok, H. H., Gotz, R. S. (2004), “Synthesis of a silk-inspired peptide oligothiophene conjugate”Org. Biomolecul. Chem. 2, 24, 3541-3044.
[17] Daly, W. H. & Poche, D., (1988), “Synthesis of a PEG-b-PAsp-b-PPhe Triblock Copolymer.” Tetrahedron Lett., 29, 46, 5859-5862.
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    Estella Judith Salamula, Martin Bredenkamp, Deon Bezuidenhout, Misael Silas Nadiye-Tabbiruka. (2015). 2-(2-(Tert-Butoxycarbonyl) Propanamido) Acetic Acid ‘NCA-AG’ Synthesis, Characterization and Reaction Optimization for the Preparation. Advances in Biochemistry, 3(6), 72-76. https://doi.org/10.11648/j.ab.20150306.12

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    ACS Style

    Estella Judith Salamula; Martin Bredenkamp; Deon Bezuidenhout; Misael Silas Nadiye-Tabbiruka. 2-(2-(Tert-Butoxycarbonyl) Propanamido) Acetic Acid ‘NCA-AG’ Synthesis, Characterization and Reaction Optimization for the Preparation. Adv. Biochem. 2015, 3(6), 72-76. doi: 10.11648/j.ab.20150306.12

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    AMA Style

    Estella Judith Salamula, Martin Bredenkamp, Deon Bezuidenhout, Misael Silas Nadiye-Tabbiruka. 2-(2-(Tert-Butoxycarbonyl) Propanamido) Acetic Acid ‘NCA-AG’ Synthesis, Characterization and Reaction Optimization for the Preparation. Adv Biochem. 2015;3(6):72-76. doi: 10.11648/j.ab.20150306.12

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  • @article{10.11648/j.ab.20150306.12,
      author = {Estella Judith Salamula and Martin Bredenkamp and Deon Bezuidenhout and Misael Silas Nadiye-Tabbiruka},
      title = {2-(2-(Tert-Butoxycarbonyl) Propanamido) Acetic Acid ‘NCA-AG’ Synthesis, Characterization and Reaction Optimization for the Preparation},
      journal = {Advances in Biochemistry},
      volume = {3},
      number = {6},
      pages = {72-76},
      doi = {10.11648/j.ab.20150306.12},
      url = {https://doi.org/10.11648/j.ab.20150306.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ab.20150306.12},
      abstract = {2-(2-(tert-butoxycarbonyl) propanamido) acetic acid (NCA-AG) was for the first time prepared using a variation of the Leuchs method. All compounds were characterized using melting point, nuclear magnetic resonance (NMR), ultra violet spectroscopy (UV), Fourier transform infrared spectroscopy (FTIR) and electron spray mass spectroscopy (ESMS). The reaction was optimised to obtain the highest yield by varying the reaction conditions namely; solvent, lewis acid and temperature.},
     year = {2015}
    }
    

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    AU  - Estella Judith Salamula
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    AU  - Deon Bezuidenhout
    AU  - Misael Silas Nadiye-Tabbiruka
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    N1  - https://doi.org/10.11648/j.ab.20150306.12
    DO  - 10.11648/j.ab.20150306.12
    T2  - Advances in Biochemistry
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    JO  - Advances in Biochemistry
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    UR  - https://doi.org/10.11648/j.ab.20150306.12
    AB  - 2-(2-(tert-butoxycarbonyl) propanamido) acetic acid (NCA-AG) was for the first time prepared using a variation of the Leuchs method. All compounds were characterized using melting point, nuclear magnetic resonance (NMR), ultra violet spectroscopy (UV), Fourier transform infrared spectroscopy (FTIR) and electron spray mass spectroscopy (ESMS). The reaction was optimised to obtain the highest yield by varying the reaction conditions namely; solvent, lewis acid and temperature.
    VL  - 3
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    ER  - 

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Author Information
  • Department of Chemistry, Institute of Polymer Science Stellenbosch University, Stellenbosch, South Africa

  • Department of Chemistry, Asia International Pacific University, Muak Lek Subdistrict, Saraburi Province, Bangkok, Thailand

  • University of Cape Town, Western Cape, Biomaterial Sciences Laboratories at the Cardiovascular Research Unit (CRU), Cape Town, South Africa

  • Department of Chemistry, University of Botswana, Gabarone, Botswana

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