Acid‐Stable Ester Linkers for the Solid‐Phase Synthesis of Immobilized Peptides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00525588" target="_blank" >RIV/61388963:_____/20:00525588 - isvavai.cz</a>
Result on the web
<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202000246" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202000246</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cplu.202000246" target="_blank" >10.1002/cplu.202000246</a>
Alternative languages
Result language
angličtina
Original language name
Acid‐Stable Ester Linkers for the Solid‐Phase Synthesis of Immobilized Peptides
Original language description
A series of N‐terminally Fmoc‐protected linkers of the general formula Fmoc‐X−CO−O−Y−COOH have been prepared, where X is −NH−CH2−CH2‐ or ‐p‐(aminomethyl)phenyl‐ and Y is −(CH2)n− (n is 1 or 4) or ‐p‐(methyl)phenyl‐. These linkers can easily be covalently attached via their C‐terminal carboxyl group to a resin bearing a free amino group. After cleavage of the N‐terminal Fmoc group, the linkers can be extended by standard solid‐phase peptide synthesis techniques. These ester linkers are acid‐stable and resistant to the base‐mediated diketopiperazine formation that often occurs during the synthesis of ester‐bound peptides, they are stable at neutral pH in aqueous buffers for days but can be effectively cleaved with 0.1 m NaOH or aq. ammonia within minutes or hours, respectively. These properties make these ester handles well suited for use as linkers for the solid‐phase peptide synthesis of immobilized peptides when the stable on‐resin immobilization of the peptides and the testing of their biological properties in aqueous buffers at neutral pH are necessary.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/EF16_019%2F0000729" target="_blank" >EF16_019/0000729: Chemical biology for drugging undruggable targets</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemPlusChem
ISSN
2192-6506
e-ISSN
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Volume of the periodical
85
Issue of the periodical within the volume
6
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
1297-1306
UT code for WoS article
000544057700024
EID of the result in the Scopus database
2-s2.0-85086744007