TY - JOUR
T1 - Accelerated Multiphosphorylated Peptide Synthesis
AU - Grunhaus, Dana
AU - Molina, Estefanía Rossich
AU - Cohen, Roni
AU - Stein, Tamar
AU - Friedler, Assaf
AU - Hurevich, Mattan
N1 - Publisher Copyright:
© 2022 The Authors. Published by American Chemical Society.
PY - 2022/8/19
Y1 - 2022/8/19
N2 - Preparing phosphorylated peptides with multiple adjacent phosphorylations is synthetically difficult, leads to β-elimination, results in low yields, and is extremely slow. We combined synthetic chemical methodologies with computational studies and engineering approaches to develop a strategy that takes advantage of fast stirring, high temperature, and a very low concentration of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to produce multiphosphorylated peptides at an extremely rapid time and high purity.
AB - Preparing phosphorylated peptides with multiple adjacent phosphorylations is synthetically difficult, leads to β-elimination, results in low yields, and is extremely slow. We combined synthetic chemical methodologies with computational studies and engineering approaches to develop a strategy that takes advantage of fast stirring, high temperature, and a very low concentration of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to produce multiphosphorylated peptides at an extremely rapid time and high purity.
KW - acceleration
KW - kinetics
KW - peptide
KW - phosphorylation
KW - solid phase synthesis
UR - http://www.scopus.com/inward/record.url?scp=85135223284&partnerID=8YFLogxK
U2 - 10.1021/acs.oprd.2c00164
DO - 10.1021/acs.oprd.2c00164
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C2 - 36032360
AN - SCOPUS:85135223284
SN - 1083-6160
VL - 26
SP - 2492
EP - 2497
JO - Organic Process Research and Development
JF - Organic Process Research and Development
IS - 8
ER -