Synthesis of a hexasaccharide partial sequence of hyaluronan for click chemistry and more

Abstract

SummaryIn the present work, the synthesis of a hexasaccharide partial sequence of hyaluronan equipped with a terminal azido moiety is reported. This hexasaccharide can be used for the attachment on surfaces by means of click chemistry and after suitable deprotection for biophysical studies.

Synthesis and In Vivo PET Imaging of Hyaluronan Conjugates of Oligonucleotides

“…Hyaluronan hexasaccharide has been previously synthesized by several slightly different strategies. − In addition, hyaluronan oligomers have been successfully assembled from dimeric building blocks on a solid support . The solution phase methods fall in two categories: either the glucuronic acid unit is introduced as a carboxy ester, ,, or the disarming carboxy function is generated by oxidation after assembly of the hexasaccharide. , The amino function has been protected with the trichloroacetyl, , phthaloyl, , or 2,2,2-trichloroethoxycarbonyl group. A thioglycoside − , or trichloroacetimidate method has been applied to the assembly of the hexasaccharide from disaccharide donors.…”

“…The solution phase methods fall in two categories: either the glucuronic acid unit is introduced as a carboxy ester, ,, or the disarming carboxy function is generated by oxidation after assembly of the hexasaccharide. , The amino function has been protected with the trichloroacetyl, , phthaloyl, , or 2,2,2-trichloroethoxycarbonyl group. A thioglycoside − , or trichloroacetimidate method has been applied to the assembly of the hexasaccharide from disaccharide donors. Based on these previous studies, we prepared the 1 - O -(3-azidopropyl) derivative of hyaluronan hexasaccharide as depicted in Schemes and .…”

“…25,28 The amino function has been protected with the trichloroacetyl, 26,27 phthaloyl, 25,28 or 2,2,2-trichloroethoxycarbonyl 29 group. A thioglycoside [25][26][27]29 or trichloroacetimidate 28 method has been applied to the assembly of the hexasaccharide from disaccharide donors. Based on these previous studies, we prepared the 1-O-(3-azidopropyl) derivative of hyaluronan hexasaccharide as depicted in Schemes 1 and 2.…”

Multivalency as a chemical organization and action principle

“…The influence of spacer length and flexibility on the binding affinity of ligands [ 6 ] will be examined as well as the mechanical stability of complexes [ 7 ]. Furthermore, the Thematic Series covers the synthesis of various new glycoarchitectures for multivalent interactions [ 8 – 12 ] and studies the scope of multivalent lectin-glycointeractions in galectins [ 13 ], with iminosugars [ 14 ] and carbohydrate mimetics [ 15 ]. This Thematic Series in the Beilstein Journal of Organic Chemistry also investigates the enhanced multivalent binding of protein scaffolds [ 16 ], peptide–polymer interactions [ 17 – 20 ] tripodal-catecholates [ 21 ] and polycatechol–surface interactions [ 22 ] as well as multivalent organocatalyts [ 23 ].…”