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- Title
Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling.
- Authors
Tokairin, Yoshinori; Soloshonok, Vadim A.; Moriwaki, Hiroki; Konno, Hiroyuki
- 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.
- Subjects
ASYMMETRIC synthesis; MICHAEL reaction; THREONINE; STRUCTURAL components
- Publication
Amino Acids, 2019, Vol 51, Issue 3, p419
- ISSN
0939-4451
- Publication type
Article
- DOI
10.1007/s00726-018-2677-5