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Beilstein J. Org. Chem. 2016, 12, 1939–1948, doi:10.3762/bjoc.12.183
Graphical Abstract
Figure 1: cis- and trans rotamer of protected PNA building blocks 1a–d and 2a–d.
Figure 2: cis- and trans rotamer of unprotected PNA-building block 3.
Figure 3: Rotameric structures of dimeric PNA glycoconjugate 4.
Scheme 1: Synthesis of building blocks 1a–d and 2a–d (a stands for D-glucose, b stands for D-galactose, c sta...
Scheme 2: Synthesis of building block 3.
Scheme 3: Synthesis of the dimeric glycoconjugate 4.
Figure 4: 1H NMR (400 MHz) of building block 1a in CDCl3. The amide signals of the rotamers are marked.
Figure 5: 1H NMR (400 MHz) of building block 1b in CDCl3. The amide signals of the rotamers are marked.
Figure 6: 1H NMR (400 MHz) of PNA glycoconjugate 4 in CDCl3. The amide signals of the rotamers of 4 (2 double...
Figure 7: Building block 1a in CDCl3, DMSO-d6, DMF-d7 and chlorobenzene-d5.
Figure 8: Temperature-dependent 1H NMR (600 MHz) spectra of building block 1a in DMSO-d6.
Figure 9: Temperature-dependent 1H NMR (600 MHz) spectra of building block 1a in chlorobenzene-d5, broadened ...
Figure 10: Temperature-dependent 1H NMR (600 MHz) spectra of building block 1b in chlorobenzene-d5, broadened ...
Figure 11: Temperature-dependent 1H NMR (600 MHz) spectra of dimeric glycoconjugate 4 in chlorobenzene-d5, bro...
Figure 12: A) Missing correlation between the amidic proton and the methylene or 2-aminoethyl protons of the P...
Beilstein J. Org. Chem. 2014, 10, 2453–2460, doi:10.3762/bjoc.10.256
Figure 1: Malonyl-linked aromatic glycoconjugate building blocks for spot synthesis of combinatorial glycopep...
Scheme 1: Synthesis of the aromatic backbone building blocks 7 and 9.
Scheme 2: Synthesis of dimers 17, 20, 22 and 24.