Synthesis, Table of Contents Synthesis 2018; 50(23): 4690-4694DOI: 10.1055/s-0037-1610221 paper © Georg Thieme Verlag Stuttgart · New York Stereoselective Synthesis of d 4-(S)-Lysine from (S)-Serine Michael Kohr Universität des Saarlandes, Organische Chemie, 66123 Saarbrücken, Germany Email: u.kazmaier@mx.uni-saarland.de , Uli Kazmaier * Universität des Saarlandes, Organische Chemie, 66123 Saarbrücken, Germany Email: u.kazmaier@mx.uni-saarland.de › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Tetradeuterated (S)-lysine can easily be obtained from protected (S)-serine in a few steps including a Cu-mediated cross coupling and subsequent platinum-catalysed deuteration. Key words Key wordsamino acids - copper - cross coupling - deuteration - isotope labelling - lysine Full Text References References Reviews: 1a Bantscheff M. Schirle M. Sweetman G. Rick J. Kuster B. Anal. Bioanal. Chem. 2007; 389: 1017 1b Chahrour O. Cobice D. Malone J. J. Pharm. Biomed. Anal. 2015; 113: 2 1c Schulze WX. Usadel B. Annu. Rev. Plant. Biol. 2010; 61: 491 1d Han X. Aslanian A. Yates JR. III. Curr. Opin. Chem. Biol. 2008; 12: 483 2 Markley JL. Brüschweiler R. Edison AS. Eghbalnia HR. Powers R. Raftery D. Wishart DS. Curr. Opin. Biotechnol. 2017; 43: 34 3a Garson MJ. Chem. Rev. 1993; 93: 1699 3b Nicolaou KC. Nevalainen M. Safina BS. Zak M. Bulat S. Angew. Chem. Int. Ed. 2002; 41: 1941; Angew. Chem. 2002, 114, 2021 3c Moody CJ. Hughes RA. Thompson SP. Alcaraz C. Chem. Commun. 2002; 1760 3d Bass PD. Gubler DA. Judd TC. Williams RM. Chem. Rev. 2013; 113: 6816 4a Kazmaier U. J. Org. Chem. 1996; 61: 3694 4b Kazmaier U. Schneider C. Synlett 1996; 975 4c Kazmaier U. Schneider C. Synthesis 1998; 1321 4d Mues H. Kazmaier U. Synthesis 2001; 487 5a Ullrich A. Chai Y. Pistorius D. Elnakady YA. Herrmann JE. Weissman KJ. Kazmaier U. Müller R. Angew. Chem. Int. Ed. 2009; 47: 4422; Angew. Chem. 2009, 121, 4486 5b Ullrich A. Herrmann J. Müller R. Kazmaier U. Eur. J. Org. Chem. 2009; 6367 5c Karmann L. Schulz K. Herrman JK. Kazmaier U. Angew. Chem. Int. Ed. 2015; 54, 4502; Angew. Chem. 2015, 127, 4585 5d Barbie P. Kazmaier U. Org. Lett. 2016; 18: 204 6a Deska J. Hähn S. Kazmaier U. Org. Lett. 2011; 13: 3210 6b Barbie P. Huo L. Müller R. Kazmaier U. Org. Lett. 2012; 14: 6064 7 Chai Y. Pistorius D. Ullrich A. Weissman KJ. Kazmaier U. Müller R. Chem. Biol. 2010; 17: 296 8a Matthews HR. Matthews KS. Opella SJ. Biochim. Biophys. Acta 1977; 497: 1 8b August RA. Khan JA. Moody CM. Young DW. Tetrahedron Lett. 1992; 33: 4617 8c Kelly NM. Sutherland A. Willis CL. Nat. Prod. Rep. 1997; 14: 205 9a Rose JE. Leeson PD. Gani D. J. Chem. Soc., Perkin Trans. 1 1992; 1563 9b Kelly NM. Reid RG. Willis CL. Winton PL. Tetrahedron Lett. 1995; 36: 8315 10 Yonaha K. Soda K. Adv. Biochem. Eng. Biotechnol. 1986; 33: 95 11a Oba M. Ueno R. Fukuoka M. Kainosho M. Nishiyama K. J. Chem. Soc., Perkin Trans. 1 1995; 1603 11b Ducho C. Hamed RB. Batchelar ET. Sorensen JL. Odella B. Schofield CJ. Org. Biomol. Chem. 2009; 7: 2770 12a Ego D. Beaucourt JP. Pichat L. J. Labelled Comp. Radiopharm. 1986; 23: 229 12b Havliček L. Hanuš J. Radioisotopy 1988; 29: 157 13 Dorokhova EM. Zolotarev YA. Kozik VS. Penkina VI. Myasoedov NF. Radioisotopy 1990; 31: 40 14a Jackson RF. W. James K. Wythes MJ. Wood A. J. Chem. Soc., Chem. Commun. 1989; 644 14b Rilatt I. Caggiano L. Jackson RF. W. Synlett 2005; 2701 14c Ross AJ. Lang HL. Jackson RF. W. J. Org. Chem. 2010; 75: 245 15 Jackson RF. W. Dexter CS. Hunter C. J. Org. Chem. 2000; 65: 7417 16a Knochel P. Yeh MC. P. Berk SC. Talbert J. J. Org. Chem. 1988; 53: 2392 16b Knochel P. Almena Perea JJ. Jones P. Tetrahedron 1998; 54: 8275 17 Newhouse T. Lewis CA. Baran PS. J. Am. Chem. Soc. 2009; 131: 6360 18 Hunt TA. Parsons AF. Pratt R. J. Org. Chem. 2006; 71: 3656 19 Jeon H.-B. Seyre LM. Biochem. Biophys. Res. Commun. 2003; 304: 788 20 Odani T. Okada S. Kabuto C. Kimura T. Shimada S. Matsuda H. Oikawa H. Matsumoto A. Nakanishi H. Cryst. Growth Des. 2009; 9: 3481 21 Yamamoto K. Bruun T. Kim JY. Zhang L. Lautens M. Org. Lett. 2016; 18: 2644 Supplementary Material Supplementary Material Supporting Information
