Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor.
The total synthesis of natural (+)-trachyspic acid and its enantiomer is described starting from a common 2-deoxy-d-ribose derivative. The synthesis of the corresponding C3 epimers from the same starting material is also described. Each stereoisomer was assayed for heparanase inhibition.
Zammit
Steven C
SC
School of Chemistry, Bio21 Institute, 30 Flemington Rd, The University of Melbourne, Victoria 3010, Australia.
Ferro
Vito
V
Hammond
Edward
E
Rizzacasa
Mark A
MA
D018360:Crystallography, X-Ray; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005966:Glucuronidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D000099175:Heparanase
D004791:Enzyme Inhibitors; D005966:Glucuronidase; D013141:Spiro Compounds; D000099175:Heparanase; C094346:trachyspic acid