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Novel synthesis of α-PNA monomers by U-4CR

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Summary.

A novel synthesis of α-PNA monomers was carried out by U-4CR, followed by photochemical cleavage of the 2-nitrobenzyl group and selective hydrolysis in the presence of 10% HCl in THF. Three of four functional components in the U-4CR were specially protected: cyclohexenyl isocyanide, Boc for protecting the amino group of glycine, and 2-nitrobenzyl group as a photocage (photoremovable protecting group) for ammonia. The amino group of aldehyde-containing adenine is too weak to interfere with the U-4CR, so that it is not necessary to be protected.

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Authors and Affiliations

  1. Department of Chemistry, National Cheng Kung University, Tainan, Taiwan, ROC

    P.-C. Huang, G.-J. Hsu, B.-R. Zhuang & K. Sung

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  1. P.-C. Huang
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  2. G.-J. Hsu
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  3. B.-R. Zhuang
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  4. K. Sung
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Authors’ address: Kuangsen Sung, Department of Chemistry, National Cheng Kung University, Tainan, Taiwan, ROC

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Huang, PC., Hsu, GJ., Zhuang, BR. et al. Novel synthesis of α-PNA monomers by U-4CR. Amino Acids 34, 449–453 (2008). https://doi.org/10.1007/s00726-007-0548-6

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  • DOI: https://doi.org/10.1007/s00726-007-0548-6

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