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Synlett 1994; 1994(11): 922-924
DOI: 10.1055/s-1994-23049
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Methylsulfonylethyloxycarbonyl Group as a Protection for the Guanidino Function in Arginine

D. Filippov* , G. A. van der Marel, E. Kuyl-Yeheskiely, J. H. van Boom
  • *Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands
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Publikationsdatum:
22. März 2002 (online)

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The side chain of arginine can be protected with two urethane methylsulfonylethyloxycarbonyl (Msc) groups, the removal of which proceeds readily and quantitatively with sodium hydroxide. The usefulness of the Msc-concept is exemplified by solution synthesis of H-Arg-Ala-OH and H-Phe-Arg-Ala-OH employing Boc-Arg(Msc)2-OH as a building unit.