Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors

Three homochiral polyhydroxylated piperidines containing a quaternary carbon branch at C‐2 of the heterocyclic ring, which can be considered as branched analogues of deoxymannorijimycin (DMJ), and their corresponding lactams were synthesised from readily available and versatile carbohydrate lactones containing a 2‐C‐hydroxymethyl branch. The key step in the synthesis of these iminosugars, 1,5‐dideoxy‐2‐C‐hydroxymethyl‐1,5‐imino‐D‐mannitol, 1,5‐dideoxy‐2‐C‐hydroxymethyl‐1,5‐imino‐L‐gulitol and 1,5‐dideoxy‐2‐C‐hydroxymethyl‐1,5‐imino‐D‐talitol, was an efficient modified Kiliani reaction performed on the readily available ketose starting materials L‐sorbose and D‐fructose. The introduction of the carbon branch at C‐2 resulted in loss of glycosidase inhibitory activity, which could be advantageous for therapeutic use of such compounds as chaperones.

show abstract

Carbohydrate-Processing Enzymes of the Lysosome

Stütz¹,

Wrodnigg²

2016

Advances in Carbohydrate Chemistry and Biochemistry

View full text Add to dashboard Cite

Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors

Abstract: 2, and the enantiomeric LRBNAc were prepared as potential hexosaminidase inhibitors from L-and D-lyxonolactone, respectively. Neither N-benzyl-DRBNAc nor N-benzyl-LRBNAc showed any inhibition of aor b-hexosaminidases or any other glycosidase.

Cited by 5 publications

References 63 publications

Scalable Syntheses of Both Enantiomers of DNJNAc and DGJNAc from Glucuronolactone: The Effect of N‐Alkylation on Hexosaminidase Inhibition

Scalable Syntheses of Both Enantiomers of DNJNAc and DGJNAc from Glucuronolactone: The Effect of N‐Alkylation on Hexosaminidase Inhibition

Carbohydrate-Processing Enzymes of the Lysosome

Contact Info

Product

Resources

About