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

0525588 - ÚOCHB 2021 RIV DE eng J - Článek v odborném periodiku
Pícha, Jan - Buděšínský, Miloš - Mitrová, Katarína - Jiráček, Jiří
Acid‐Stable Ester Linkers for the Solid‐Phase Synthesis of Immobilized Peptides.
ChemPlusChem. Roč. 85, č. 6 (2020), s. 1297-1306. ISSN 2192-6506. E-ISSN 2192-6506
Grant CEP: GA MŠMT(CZ) EF16_019/0000729
Institucionální podpora: RVO:61388963
Klíčová slova: diketopiperazines * esters * peptides * protecting groups * solid-phase synthesis
Obor OECD: Organic chemistry
Impakt faktor: 2.863, rok: 2020
Způsob publikování: Omezený přístup
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202000246

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.
Trvalý link: http://hdl.handle.net/11104/0309699