Palladium mediated deallylation in fully aqueous conditions for native chemical ligation at aspartic and glutamic acid sites

Muhammad Jbara; Emad Eid; Ashraf Brik

doi:10.1039/c8ob00890f

Palladium mediated deallylation in fully aqueous conditions for native chemical ligation at aspartic and glutamic acid sites

Muhammad Jbara, Emad Eid, Ashraf Brik^*

^*Corresponding author for this work

Technion-Israel Institute of Technology

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

20 Scopus citations

Abstract

An efficient native chemical ligation approach at Asp and Glu sites is reported applying a hydrazide precursor, as a peptide thioester, and allyl protection at the side chain of Asp and Glu. The allyl protection was efficiently removed, after the ligation step, using the water-soluble palladium complex [Pd(allyl)Cl]₂ and glutathione within a few minutes under fully aqueous conditions.

Original language	English
Pages (from-to)	4061-4064
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	22
DOIs	https://doi.org/10.1039/c8ob00890f
State	Published - 2018
Externally published	Yes

Funding

Funders	Funder number
Planning and Budgeting Committee of the Council for Higher Education of Israel

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abstract = "An efficient native chemical ligation approach at Asp and Glu sites is reported applying a hydrazide precursor, as a peptide thioester, and allyl protection at the side chain of Asp and Glu. The allyl protection was efficiently removed, after the ligation step, using the water-soluble palladium complex [Pd(allyl)Cl]2 and glutathione within a few minutes under fully aqueous conditions.",

author = "Muhammad Jbara and Emad Eid and Ashraf Brik",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

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AU - Jbara, Muhammad

AU - Eid, Emad

AU - Brik, Ashraf

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AB - An efficient native chemical ligation approach at Asp and Glu sites is reported applying a hydrazide precursor, as a peptide thioester, and allyl protection at the side chain of Asp and Glu. The allyl protection was efficiently removed, after the ligation step, using the water-soluble palladium complex [Pd(allyl)Cl]2 and glutathione within a few minutes under fully aqueous conditions.

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Palladium mediated deallylation in fully aqueous conditions for native chemical ligation at aspartic and glutamic acid sites

Abstract

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