Beilstein J. Org. Chem.2017,13, 1222–1229, doi:10.3762/bjoc.13.121
-anhydro-α-L-galactopyranose unit (naturally present in the agarose structure) to all glycamines synthesized, constituting an amino-substituted C-threofuranoside moiety, which is closely related to (+)-muscarine.
Keywords: amino sugar; 3,6-anhydro-α-L-galactopyranose; polysaccharide (agar); protecting
(1→3)-β-D-galactopyranose-(1→4)-3,6-anhydro-α-L-galactopyranose [1]. Both 1 and its less refined versions (agar or agar-agar) are well known due to their wide applications in food industry, microbiology and laboratorial sciences [2][3]. Even though agar and pure 1 are readily and commercially
available, these polysaccharides are far little explored as sources of chemical platforms for drug development. The rare monosaccharide 3,6-anhydro-α-L-galactopyranose (AnGal), naturally present in the agarose structure, is a valuable scaffold since it is a highly functionalized and a chiral-rich monomer
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Graphical Abstract
Scheme 1:
Overview of the hydrolysis–reductive amination procedure to produce primary glycamine 3 and byprodu...