Facile synthesis of alpha,alpha-diisobutylglycine and anchoring its derivatives onto PAL-PEG-PS resin.
alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N(alpha)-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.
Fu
Yanwen
Y
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Etienne
Marcus A
MA
Hammer
Robert P
RP
D000085:Acetates / Q000737:chemistry*; D000478:Alkylation; D000812:Anhydrides / Q000737:chemistry; D002073:Butanes / Q000138:chemical synthesis*; D000440:Butanols / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry; D010455:Peptides / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry*
D000085:Acetates; D000812:Anhydrides; D002073:Butanes; D000440:Butanols; D010455:Peptides; D020005:Propanols; D012117:Resins, Synthetic; C482838:alpha,alpha-diisobutylglycine; C006463:allyl alcohol; C040507:isobutyl alcohol; D010165:Palladium; C028257:nitroacetic acid; D005998:Glycine