Synthesis of sialyl lewis x mimetics as selectin inhibitors by enzymatic aldol condensation reactions

Study of real-time lectin–carbohydrate interactions on the surface of a quartz crystal microbalance

“…Allyl-␣-d-mannopyranoside was synthesised according to a previously described protocol by camphorsulfonic acidcatalyzed coupling of allyl alcohol to unprotected d-mannose (Lin et al, 1999). Viscum album agglutinin (mistletoe lectin, VAA) was a kind gift from Prof. Hans-Joachim Gabius, Ludwig-Maximilians University, Munich, Germany.…”

The synthesis of d-C-mannopyranosides

“…With the methyl 2,3,4,6-tetra-O-benzylmannopyranoside derivative 11, allylation in the anomeric position, selective protecting group removal in position 6, and subsequent acetylation is possible in good yield (Scheme 22) [50,53,140,141].…”

“…It has also been incorporated in synthetic entities such as modified glycosyl amino-acids [31][32][33][34][35], or used in the course of total syntheses, that is a guanofosfocin analogue, for chitine synthase inhibition [36], (À)-daucic acid [37,38], zooxanthellatoxins [39] and the IJK ring framework of brevetoxin B [40]. Various D-Cmannopyranoside derivatives have been synthesized in order to evaluate their biological activity as lectin inhibitors relative to their O-glycoside counterpart [41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57]. C-mannosides have also been prepared and tested as potential glycosidase and glycosyltransferase inhibitors [58][59][60][61][62][63][64], as anti-inflammatory derivatives [65], anti-tumor agents [30,66], and anti-bacterial agents [67,68].…”

Enantioselective C–C bond synthesis catalysed by enzymes

“…It was thus possible to synthesise three of the four diastereoisomers enantioselectively (Scheme 20). 35 The only remaining diastereoisomer that was not prepared has the L-erythro stereochemistry. Unfortunately the aldolase that might catalyse its formation, tagatose 1,6-diphosphate aldolase (TDP A), is not very stereoselective and therefore often yields mixtures of diastereoisomers.…”