C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles

TY - JOUR

T1 - C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles

AU - Hansen, Jonas

AU - Diness, Frederik

AU - Meldal, Morten Peter

PY - 2016

Y1 - 2016

N2 - A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.

AB - A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.

U2 - 10.1039/c6ob00213g

DO - 10.1039/c6ob00213g

M3 - Journal article

C2 - 26924021

SN - 1477-0520

VL - 14

SP - 3238

EP - 3245

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 12

ER -