Synthesis of stereoarray isotope labeled (SAIL) lysine via the "head-to-tail" conversion of SAIL glutamic acid.
A stereoarray isotope labeled (SAIL) lysine, (2S,3R,4R,5S,6R)-[3,4,5,6-(2)H(4);1,2,3,4,5,6-(13)C(6);2,6-(15)N(2)]lysine, was synthesized by the "head-to-tail" conversion of SAIL-Glu, (2S,3S,4R)-[3,4-(2)H(2);1,2,3,4,5-(13)C(5);2-(15)N]glutamic acid, with high stereospecificities for all five chiral centers. With the SAIL-Lys in hand, the unambiguous simultaneous stereospecific assignments were able to be established for each of the prochiral protons within the four methylene groups of the Lys side chains in proteins.
Center for Priority Areas, Tokyo Metropolitan University, 1-1 minami-ohsawa, Hachioji, Tokyo, 192-0397, Japan.
Tsutomu
T
Terauchi
Tomoe
T
Kamikawai
Maxim G
MG
Vinogradov
Eugenia V
EV
Starodubtseva
Mitsuhiro
M
Takeda
Masatsune
M
Kainosho
D018698:Glutamic Acid / Q000737:chemistry*; D008239:Lysine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D018698:Glutamic Acid; D008239:Lysine