Accelerated Multiphosphorylated Peptide Synthesis

Dana Grunhaus; Estefanía Rossich Molina; Roni Cohen; Tamar Stein; Assaf Friedler; Mattan Hurevich

doi:10.1021/acs.oprd.2c00164

Accelerated Multiphosphorylated Peptide Synthesis

Institute of Chemistry

The Hebrew University of Jerusalem

Research output: Contribution to journal › Review article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2492-2497
Number of pages	6
Journal	Organic Process Research and Development
Volume	26
Issue number	8
DOIs	https://doi.org/10.1021/acs.oprd.2c00164
State	Published - 19 Aug 2022

Keywords

acceleration
kinetics
peptide
phosphorylation
solid phase synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.oprd.2c00164

Cite this

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title = "Accelerated Multiphosphorylated Peptide Synthesis",

abstract = "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.",

keywords = "acceleration, kinetics, peptide, phosphorylation, solid phase synthesis",

author = "Dana Grunhaus and Molina, \{Estefan{\'i}a Rossich\} and Roni Cohen and Tamar Stein and Assaf Friedler and Mattan Hurevich",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

year = "2022",

month = aug,

day = "19",

doi = "10.1021/acs.oprd.2c00164",

language = "English",

volume = "26",

pages = "2492--2497",

journal = "Organic Process Research and Development",

issn = "1083-6160",

publisher = "American Chemical Society",

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}

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

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 - https://www.scopus.com/pages/publications/85135223284

U2 - 10.1021/acs.oprd.2c00164

DO - 10.1021/acs.oprd.2c00164

M3 - Review article

C2 - 36032360

SN - 1083-6160

VL - 26

SP - 2492

EP - 2497

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 8

ER -

Accelerated Multiphosphorylated Peptide Synthesis

Abstract

Keywords

ASJC Scopus subject areas

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