Acid‐Stable Ester Linkers for the Solid‐Phase Synthesis of Immobilized Peptides

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Acid‐Stable Ester Linkers for the Solid‐Phase Synthesis of Immobilized Peptides

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Acid‐Stable Ester Linkers for the Solid‐Phase Synthesis of Immobilized Peptides

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/EF16_019%2F0000729" target="_blank" >EF16_019/0000729: Chemická biologie pro vývoj nových terapií</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ChemPlusChem

ISSN

2192-6506

e-ISSN

—

Svazek periodika

85

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

1297-1306

Kód UT WoS článku

000544057700024

EID výsledku v databázi Scopus

2-s2.0-85086744007