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Beilstein J. Org. Chem. 2017, 13, 2169–2178, doi:10.3762/bjoc.13.217
Graphical Abstract
Scheme 1: Retrosynthesis of the Pro–Pro DKP framework.
Scheme 2: Coupling with N-hydroxysuccinimide-activated amino acids.
Scheme 3: Synthesis of Pro–Pro DKP.
Scheme 4: Synthesis of substituted Pro–Pro DKP 15a.
Scheme 5: Potential isomers yielded by cyclization of 16.
Figure 1: Optimized geometries for the two conformers presenting interactions with either Ca (16a) or Cb (16b...
Figure 2: Optimized geometries of the extrema located along the pathway for formation of 15a with explicit pa...
Figure 3: Optimized geometries of the extrema located along the pathway for formation of 15b with explicit pa...
Figure 4: Optimized geometries for the transition states associated to alternate position of the methanol mol...
Scheme 6: Synthesis of diketopiperazine 19.
Beilstein J. Org. Chem. 2017, 13, 2087–2093, doi:10.3762/bjoc.13.206
Figure 1: Structure of the VVIA peptide.
Scheme 1: Synthesis of Boc-VVIA-OBn by the ball-milling approach.
Scheme 2: Synthesis of tetrapeptide Boc-VVIA-OBn in solution.
Scheme 3: Synthesis of TFA·H-VVIA-OH by SPPS.
Figure 2: Comparison of the reaction time of the coupling steps performed in the BM and in solution.