El CRAI romandrà tancat del 24 de desembre de 2025 al 6 de gener de 2026. La validació de documents es reprendrà a partir del 7 de gener de 2026.
El CRAI permanecerá cerrado del 24 de diciembre de 2025 al 6 de enero de 2026. La validación de documentos se reanudará a partir del 7 de enero de 2026.
From 2025-12-24 to 2026-01-06, the CRAI remain closed and the documents will be validated from 2026-01-07.
 
Miniatura

Fitxers

681055.pdf (2.51 MB)

Tipus de document

Article

Versió

Versió publicada

Data de publicació

2016-11-15

Llicència de publicació

cc-by (c) Luna, Omar F. et al., 2016
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/151704

Deprotection reagents in Fmoc solid phase peptide synthesis: Moving away from piperidine?

Títol de la revista

Autors

Director/Tutor

ISSN de la revista

Títol del volum

Recurs relacionat

https://doi.org/10.3390/molecules21111542

Resum

The deprotection step is crucial in order to secure a good quality product in Fmoc solid phase peptide synthesis. 9-Fluorenylmethoxycarbonyl (Fmoc) removal is achieved by a two-step mechanism reaction favored by the use of cyclic secondary amines; however, the efficiency of the reaction could be affected by side reactions and by-product formation. Several aspects have to be taken into consideration when selecting a deprotection reagent: its physicochemical behavior, basicity (pKa) and polarity, concentration, and time of reaction, toxicity and disposability of residues and, finally, availability of reagents. This report presents a comparison of the performance of three strategies for deprotection using microwave-assisted Fmoc peptide synthesis. Four peptide sequences were synthesized using Rink amide resin with a Liberty Blue automated synthesizer and 4-methylpiperidine (4MP), piperidine (PP), and piperazine (PZ) as Fmoc removal reagents. In the first instance all three reagents behaved similarly. A detailed analysis showed a correlation between the hydrophobicity and size of the peptide with the yield and purity of the obtained product. The three reagents are interchangeable, and replacement of piperidine could be advantageous regarding toxicity and reagent handling.

Matèries

Síntesi de pèptids, Amines

Matèries (anglès)

Peptide synthesis, Amines

Citació

Col·leccions

Articles publicats en revistes (Química Inorgànica i Orgànica)

Citació

LUNA, Omar f., GOMEZ, Johana, CARDENAS, Constanza, ALBERICIO PALOMERA, Fernando, MARSHALL, Sergio h., GUZMÁN, Fanny. Deprotection reagents in Fmoc solid phase peptide synthesis: Moving away from piperidine?. _Molecules_. 2016. Vol. 21, núm. 11, pàgs. 1542. [consulta: 25 de desembre de 2025]. ISSN: 1420-3049. [Disponible a: https://hdl.handle.net/2445/151704]

Exportar metadades

JSON - METS

Compartir registre