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Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142
Graphical Abstract
Figure 1: a) Proposed oxidative pathway for provision of GDP-ManA 5 from GDP-Man 1, C6 stereochemistry of 3 i...
Scheme 1: Syntheses of C6-modified mannose 1-phosphates 13 and 17. Conditions a) PPh3, CBr4, DCM, rt, 75%; b)...
Figure 2: Structure of 16 with ADPs rendered at the 50% probability level. Acetyl group disorder is omitted f...
Scheme 2: Evaluation of enzymatic GDP-Man synthesis using C6-modified mannose 1-phosphates 13, 17, and 18; Y+...
Figure 3: GMD function with probe 19 over 120 min (GMD (100 µg/mL), GDP sugars (50 µM), NAD+ (200 µM)). Dotte...
Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110
Figure 1: a) Chemical structure of alginate showing constituent M and G residues and C2/C3 acetylation for on...
Scheme 1: a) H2N(CH2)2CN, PyBOP, DIPEA, CH2Cl2, 0 °C, 40 min, 47% (+44% 3); b) TBSOTf, imidazole, DMAP, DMF, ...
Scheme 2: a) BzCl, DMAP, pyridine, CH2Cl2, rt, 24 h, 90%; b) TBSOTf, imidazole, DMAP, DMF, 40 °C, 24 h, 78%; ...
Scheme 3: a) PMBCl, KI, K2CO3, DMF, rt, 53% for 11 and 12; b) BnBr, DMF, Et3N, DCM, rt, 31% for 13 and 14.
Scheme 4: a) DMSO, SO3·pyridine, Et3N, rt, 1 h, 96%; b) H2NOH·HCl, THF, H2O, Na2CO3, 89%; c) POCl3, MeCN, 65 ...