The synthesis of some peptides related to the amyloid β peptide 25-35: Use of N-(2-hydroxy-4-methoxybenzyl) protection

Omar M.A. El-Agnaf; Patrick Harriott; David J.S. Guthrie; G. Brent Irvine; Brian Walker

doi:10.1007/BF00128531

The synthesis of some peptides related to the amyloid β peptide 25-35: Use of N-(2-hydroxy-4-methoxybenzyl) protection

Omar M.A. El-Agnaf, Patrick Harriott, David J.S. Guthrie, G. Brent Irvine, Brian Walker

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

13 Citations (Scopus)

Abstract

The sequence from residues 25-35 of the amyloid β peptide has been identified as an important factor in the neurotoxicity displayed by this peptide. Attempts to synthesize analogues of this sequence using Fmoc-protected amino acids in solid phase synthesis were initially unsuccessful, with coupling stopping after Ala³⁰. By incorporating N-(2-hydroxy-4-methoxybenzyl)alanine at this position, total synthesis of the undecapeptide was accomplished. Success was also achieved by switching the synthesis to a commercial synthesiser which uses a flow system and improved solvent conditions.

Original language	English
Pages (from-to)	135-141
Number of pages	7
Journal	Letters in Peptide Science
Volume	1
Issue number	3
DOIs	https://doi.org/10.1007/BF00128531
Publication status	Published - Dec 1994
Externally published	Yes

Keywords

Alzheimer's disease
Amide protection
Conductivity
Solid phase peptide synthesis

ASJC Scopus subject areas

Biochemistry

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10.1007/BF00128531

Cite this

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title = "The synthesis of some peptides related to the amyloid β peptide 25-35: Use of N-(2-hydroxy-4-methoxybenzyl) protection",

abstract = "The sequence from residues 25-35 of the amyloid β peptide has been identified as an important factor in the neurotoxicity displayed by this peptide. Attempts to synthesize analogues of this sequence using Fmoc-protected amino acids in solid phase synthesis were initially unsuccessful, with coupling stopping after Ala30. By incorporating N-(2-hydroxy-4-methoxybenzyl)alanine at this position, total synthesis of the undecapeptide was accomplished. Success was also achieved by switching the synthesis to a commercial synthesiser which uses a flow system and improved solvent conditions.",

keywords = "Alzheimer's disease, Amide protection, Conductivity, Solid phase peptide synthesis",

author = "El-Agnaf, {Omar M.A.} and Patrick Harriott and Guthrie, {David J.S.} and Irvine, {G. Brent} and Brian Walker",

year = "1994",

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T1 - The synthesis of some peptides related to the amyloid β peptide 25-35

T2 - Use of N-(2-hydroxy-4-methoxybenzyl) protection

AU - El-Agnaf, Omar M.A.

AU - Harriott, Patrick

AU - Guthrie, David J.S.

AU - Irvine, G. Brent

AU - Walker, Brian

PY - 1994/12

Y1 - 1994/12

N2 - The sequence from residues 25-35 of the amyloid β peptide has been identified as an important factor in the neurotoxicity displayed by this peptide. Attempts to synthesize analogues of this sequence using Fmoc-protected amino acids in solid phase synthesis were initially unsuccessful, with coupling stopping after Ala30. By incorporating N-(2-hydroxy-4-methoxybenzyl)alanine at this position, total synthesis of the undecapeptide was accomplished. Success was also achieved by switching the synthesis to a commercial synthesiser which uses a flow system and improved solvent conditions.

AB - The sequence from residues 25-35 of the amyloid β peptide has been identified as an important factor in the neurotoxicity displayed by this peptide. Attempts to synthesize analogues of this sequence using Fmoc-protected amino acids in solid phase synthesis were initially unsuccessful, with coupling stopping after Ala30. By incorporating N-(2-hydroxy-4-methoxybenzyl)alanine at this position, total synthesis of the undecapeptide was accomplished. Success was also achieved by switching the synthesis to a commercial synthesiser which uses a flow system and improved solvent conditions.

KW - Alzheimer's disease

KW - Amide protection

KW - Conductivity

KW - Solid phase peptide synthesis

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ER -

The synthesis of some peptides related to the amyloid β peptide 25-35: Use of N-(2-hydroxy-4-methoxybenzyl) protection

Abstract

Keywords

ASJC Scopus subject areas

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