Chemoselective protection of solid-phase compatible Fmoc-phosphinic building blocks

Magdalini Nasopoulou; Magdalini Matziari; Vincent Dive; Athanasios Yiotakis

doi:10.1021/jo061535z

Chemoselective protection of solid-phase compatible Fmoc-phosphinic building blocks

Magdalini Nasopoulou, Magdalini Matziari, Vincent Dive, Athanasios Yiotakis^*

^*Corresponding author for this work

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

14 Citations (Scopus)

Abstract

(Chemical Equation Presented) An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).

Original language	English
Pages (from-to)	9525-9527
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	71
Issue number	25
DOIs	https://doi.org/10.1021/jo061535z
Publication status	Published - 8 Dec 2006
Externally published	Yes

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10.1021/jo061535z

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abstract = "(Chemical Equation Presented) An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).",

author = "Magdalini Nasopoulou and Magdalini Matziari and Vincent Dive and Athanasios Yiotakis",

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AU - Nasopoulou, Magdalini

AU - Matziari, Magdalini

AU - Dive, Vincent

AU - Yiotakis, Athanasios

PY - 2006/12/8

Y1 - 2006/12/8

N2 - (Chemical Equation Presented) An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).

AB - (Chemical Equation Presented) An efficient four-step synthetic strategy able to fully discriminate hydroxyphosphinyl and carboxylic groups of Fmoc-phosphinic building blocks and related analogues has been developed. The proposed method applies selective acidic removal of the phenacyl (Pac) group from the hydroxyphosphinyl functionality and protection by the 1-adamantyl (Ad) group. Reductive removal of the Pac group from the carboxylic functionality leads to Fmoc-protected phosphinic pseudodipeptidic units suitable for phosphinic peptide and library development using solid-phase peptide synthesis (SPPS).

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Chemoselective protection of solid-phase compatible Fmoc-phosphinic building blocks

Abstract

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