TY - JOUR

T1 - Oxime ligation in acetic acid: efficient synthesis of aminooxy-peptide conjugates

AU - Chelushkin, Pavel S.

AU - Leko, Maria V.

AU - Dorosh, Marina Yu

AU - Burov, Sergey V.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Oxime ligation is a powerful tool in various bioconjugation strategies. Nevertheless, high reaction rates and quantitative yields are typically reported for aldehyde-derived compounds. In contrary, keto groups react much slower, with quantitative yields achieved at 5 h for low-molecular weight compounds and more than 15 h for polymers or dendrimers. In this communication, we report that oxime ligation proceeds rapidly with quantitative (>95%) conversion within 1.5–2 h in pure acetic acid. The practical utility of suggested technique is illustrated by the synthesis of peptide-steroid and peptide-polymer conjugates of model aminooxy-peptides.

AB - Oxime ligation is a powerful tool in various bioconjugation strategies. Nevertheless, high reaction rates and quantitative yields are typically reported for aldehyde-derived compounds. In contrary, keto groups react much slower, with quantitative yields achieved at 5 h for low-molecular weight compounds and more than 15 h for polymers or dendrimers. In this communication, we report that oxime ligation proceeds rapidly with quantitative (>95%) conversion within 1.5–2 h in pure acetic acid. The practical utility of suggested technique is illustrated by the synthesis of peptide-steroid and peptide-polymer conjugates of model aminooxy-peptides.

KW - aminooxy-peptides

KW - oxime ligation

KW - peptide-steroids conjugates

KW - polymer-peptide conjugates

UR - http://www.scopus.com/inward/record.url?scp=84994890047&partnerID=8YFLogxK

U2 - 10.1002/psc.2931

DO - 10.1002/psc.2931

M3 - Article

C2 - 27699914

AN - SCOPUS:84994890047

VL - 23

SP - 13

EP - 15

JO - Journal of Peptide Science

JF - Journal of Peptide Science

SN - 1075-2617

IS - 1

ER -