Bristol-myers Squibb Compnay

David S Nirschl

Percy H Carter

Martin D Eastgate

Mahboubeh Kheirabadi

Gardner S Creech

The disclosure is directed to the synthesis and improved methods for purifying macrocyclic peptides produced by solid phase peptide synthesis. The synthesized peptide is capped with an alkyne-functionalized or azide-functionalized compound of formula (I): prior to cleavage of the peptide from the solid phase support.

Non-chromatographic purification of macrocyclic peptides by a resin catch and release

The disclosure is directed to compounds and methods for preparing purified macrocyclic peptide using 'catch-release' methods. These methods comprise reacting a free amino group of a resin-bound linear peptide with an azide- or alkyne-functionalized cap to form a resin-bound capped linear peptide having an azide- or alkyne-functionalized cap; cleaving the capped linear peptide from the resin to form a free capped linear peptide having an azide- or alkyne-functionalized cap; reacting the free capped linear peptide having an azide-functionalized cap with an alkyne-functionalized catch resin, or reacting the free capped linear peptide having an akynyl-functionalized cap with an azide functionalized catch resin, to form a catch-resin bound capped linear peptide; reacting the catch-resin bound capped linear peptide under conditions sufficient to effect macrocyclization of the linear peptide and release of the macrocyclic peptide from the catch resin.

Growing community of inventors

Yardley, PA, United States of America

David S Nirschl