'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'.

'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'. Research Abstract Details 

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'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'. Abstract Text:

Atsuhiko Taniguchi,Taku Yoshiya,Naoko Abe,Fukue Fukao,Youhei Sohma,Tooru Kimura,Yoshio Hayashi,Yoshiaki Kiso,Atsuhiko Taniguchi,Taku Yoshiya,Naoko Abe,Fukue Fukao,Youhei Sohma,Tooru Kimura,Yoshio Hayashi,Yoshiaki Kiso,

'O-Acyl isopeptide method' is an efficient synthetic method for peptides. We designed 'O-acyl isodipeptide units', Boc-Ser/Thr(Fmoc-Xaa)-OH, as important building blocks to enable routine use of the O-acyl isopeptide method. In the synthesis of an Abeta1-42 isopeptide using O-acyl isodipeptide unit Boc-Ser(Fmoc-Gly)-OH, a side reaction, resulting in the deletion of Ser(26) in the O-acyl isopeptide structure, was noticed during coupling of the unit. We observed that the side reaction occurred during the activation step and was solvent-dependent. In DMF or NMP, an intramolecular side reaction, originating from the activated species of the unit, occurred during the activation step. In non-polar solvents such as CHCl(3) or CH(2)Cl(2), the side reaction was less likely to occur. Using CH(2)Cl(2) as solvent in coupling the unit, the target Abeta1-42 isopeptide was synthesized with almost no major side reaction.

'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'. Publishing Authors By Initials

A Taniguchi,T Yoshiya,N Abe,F Fukao,Y Sohma,T Kimura,Y Hayashi,Y Kiso,A Taniguchi,T Yoshiya,N Abe,F Fukao,Y Sohma,T Kimura,Y Hayashi,Y Kiso,

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'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of peptide science : an official publicati

VOLUME: 13

Page Numbers: 868-74

Journal Abbreviation: J. Pept. Sci.

ISSN: 1075-2617

DAY: 6

MONTH: Dec

YEAR: 2007

'O-Acyl isopeptide method' for peptide synthesis: Solvent effects in the synthesis of Abeta1-42 isopeptide using 'O-acyl isodipeptide unit'. Information

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LANGUAGE: eng

NlmUniqueID: 9506309

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AFFILIATION: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.

Country: England

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MEDLINETA: J Pept Sci

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