The potential of N-alkoxymethyl groups as peptide backbone protectants

Ana I. Fernández-Llamazares; Jan Spengler; Fernando Albericio

doi:10.1016/j.tetlet.2013.10.149

The potential of N-alkoxymethyl groups as peptide backbone protectants

Ana I. Fernández-Llamazares
, Jan Spengler
, Fernando Albericio

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

In this study, the potential of N-alkoxymethyl groups as protectants for the peptide backbone has been investigated. These groups were found to be compatible with the standard conditions of Fmoc/^tBu SPPS, and can be cleaved off from the peptide backbone by acids. Thus, backbone N-alkoxymethyl groups may be useful to prevent undesired side-reactions and/or interchain aggregation during peptide elongation on the solid-phase. However, the main issue for their application as protecting groups is the difficulty to incorporate them into the peptide backbone.

Original language	English
Pages (from-to)	184-188
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2013.10.149
State	Published - 1 Jan 2014
Externally published	Yes

Keywords

Backbone N-alkylation
Backbone protecting groups
N-Alkoxymethyl
Peptides
SPPS

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10.1016/j.tetlet.2013.10.149

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title = "The potential of N-alkoxymethyl groups as peptide backbone protectants",

abstract = "In this study, the potential of N-alkoxymethyl groups as protectants for the peptide backbone has been investigated. These groups were found to be compatible with the standard conditions of Fmoc/tBu SPPS, and can be cleaved off from the peptide backbone by acids. Thus, backbone N-alkoxymethyl groups may be useful to prevent undesired side-reactions and/or interchain aggregation during peptide elongation on the solid-phase. However, the main issue for their application as protecting groups is the difficulty to incorporate them into the peptide backbone.",

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T1 - The potential of N-alkoxymethyl groups as peptide backbone protectants

AU - Fernández-Llamazares, Ana I.

AU - Spengler, Jan

AU - Albericio, Fernando

PY - 2014/1/1

Y1 - 2014/1/1

N2 - In this study, the potential of N-alkoxymethyl groups as protectants for the peptide backbone has been investigated. These groups were found to be compatible with the standard conditions of Fmoc/tBu SPPS, and can be cleaved off from the peptide backbone by acids. Thus, backbone N-alkoxymethyl groups may be useful to prevent undesired side-reactions and/or interchain aggregation during peptide elongation on the solid-phase. However, the main issue for their application as protecting groups is the difficulty to incorporate them into the peptide backbone.

AB - In this study, the potential of N-alkoxymethyl groups as protectants for the peptide backbone has been investigated. These groups were found to be compatible with the standard conditions of Fmoc/tBu SPPS, and can be cleaved off from the peptide backbone by acids. Thus, backbone N-alkoxymethyl groups may be useful to prevent undesired side-reactions and/or interchain aggregation during peptide elongation on the solid-phase. However, the main issue for their application as protecting groups is the difficulty to incorporate them into the peptide backbone.

KW - Backbone N-alkylation

KW - Backbone protecting groups

KW - N-Alkoxymethyl

KW - Peptides

KW - SPPS

UR - https://www.scopus.com/pages/publications/84890145789

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DO - 10.1016/j.tetlet.2013.10.149

M3 - Artículo

AN - SCOPUS:84890145789

SN - 0040-4039

VL - 55

SP - 184

EP - 188

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

The potential of N-alkoxymethyl groups as peptide backbone protectants

Abstract

Keywords

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