Abstract
Practical new routes for preparation of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives, the key structural components of cytotoxic marine peptides callipeltin O and Q, suitable for the Fmoc-SPPS, were developed. (2S,3S)-Fmoc-3-Me-Gln(Xan)-OH was synthesized via Michael addition reactions of Ni (II) complex of chiral Gly-Schiff base; while Fmoc-(R)-allo-Thr-OH was prepared using chiral Ni (II) complex-assisted α-epimerization methodology, starting form (S)-Thr(tBu)-OH.
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Acknowledgements
This work was supported in part by a Grant-in-Aid from the Japan Society for the Promotion of Science (240145) to H.K. Y.T. is grateful to the Japan Society for the Promotion of Science Fellowships for young scientist (00465). V.A.S. is grateful to IKERBASQUE, the Basque Foundation for Science for financial support.
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Tokairin, Y., Soloshonok, V.A., Moriwaki, H. et al. Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling. Amino Acids 51, 419–432 (2019). https://doi.org/10.1007/s00726-018-2677-5
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DOI: https://doi.org/10.1007/s00726-018-2677-5