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

^*Corresponding author for this work

Queen's University Belfast

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

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10.1007/BF00128531

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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",

month = dec,

doi = "10.1007/BF00128531",

language = "English",

volume = "1",

pages = "135--141",

journal = "Letters in Peptide Science",

issn = "0929-5666",

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TY - JOUR

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

UR - https://www.scopus.com/pages/publications/0003363148

U2 - 10.1007/BF00128531

DO - 10.1007/BF00128531

M3 - Article

AN - SCOPUS:0003363148

SN - 0929-5666

VL - 1

SP - 135

EP - 141

JO - Letters in Peptide Science

JF - Letters in Peptide Science

IS - 3

ER -

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

Abstract

Keywords

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