Solid-phase synthesis of carboxylic and oxamic acids via OsO4/NaIO4/HMTA-mediated oxidative cleavage of acetylenic peptides.
A general method for the solid-phase synthesis of carboxy-functionalized peptides by oxidative cleavage of alkynes is presented. Clean and quantitative conversion is enabled by the addition of bases, such as DABCO and HMTA, to the classical OsO4/NaIO4 mixture. The utility of the reaction is further illustrated by the synthesis of oxamic acids.
Nielsen
Thomas E
TE
Carlsberg Laboratory, SPOCC Centre, Gamle Carlsberg Vej 10, DK-2500 Valby, Denmark.
Le Quement
Sebastian T
ST
Meldal
Morten
M
D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D009227:Myristic Acids / Q000737:chemistry*; D009993:Osmium Tetroxide / Q000737:chemistry*; D010072:Oxamic Acid / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D012974:Sodium Iodide / Q000737:chemistry*
C500253:3-hydroxy-4-methyltetradecanoic acid; D002264:Carboxylic Acids; D009227:Myristic Acids; D010455:Peptides; D012974:Sodium Iodide; D009993:Osmium Tetroxide; D010072:Oxamic Acid