Direct Solid-Phase Synthesis of the β-Amyloid (1-42) Peptide Using Controlled Microwave Heating

被引：62

作者：

Bacsa, Bernadett ^{[1
,2
,3
]}

Bosze, Szilvia ^{[3
]}

Kappe, C. Oliver ^{[1
,2
]}

机构：

[1] Karl Franzens Univ Graz, Christian Doppler Lab Microwave Chem, A-8010 Graz, Austria

[2] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

[3] Eotvos Lorand Univ, Hungarian Acad Sci, Res Grp Peptide Chem, H-1117 Budapest, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 06期

关键词：

ALZHEIMERS-DISEASE; EFFICIENT SYNTHESIS; PROTEIN TOXICITY; NEUROTOXICITY; SEQUENCES; PURIFICATION; IRRADIATION; BETA-AMYLOID(1-43); PATHOGENESIS; RACEMIZATION;

D O I：

10.1021/jo100136r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Standard linear Fmoc/t-Bu solid-phase synthesis of the 42-mer beta-amyloid (1-42) peptide was achieved under controlled microwave conditions at 86 degrees C using inexpensive DIC/HOBt as coupling reagent on ChemMatrix resin. In order to avoid racemization of the sensitive amino acids, the coupling of the three His residues in the difficult peptide sequence was performed at room temperature. The desired peptide was obtained within 15 h overall processing time in high yield and purity (78% crude yield).

引用

页码：2103 / 2106

页数：4

共 50 条

[31] Amyloid β peptide 1-42 highly correlates with capillary cerebral amyloid angiopathy and Alzheimer disease pathology
Attems, J
Lintner, F
Jellinger, KA
ACTA NEUROPATHOLOGICA, 2004, 107 (04) : 283 - 291
[32] Advances in Fmoc solid-phase peptide synthesis
Behrendt, Raymond
White, Peter
Offer, John
JOURNAL OF PEPTIDE SCIENCE, 2016, 22 (01) : 4 - 27
[33] Amyloid Fibril Formation of Arctic Amyloid-β 1-42 Peptide is Efficiently Inhibited by the BRICHOS Domain
Zhong, Xueying
Kumar, Rakesh
Wang, Yu
Biverstal, Henrik
Jegerschoeld, Caroline Ingeborg
Koeck, Philip J. B.
Johansson, Jan
Abelein, Axel
Chen, Gefei
ACS CHEMICAL BIOLOGY, 2022, 17 (08) : 2201 - 2211
[34] The effect of solvents on the conformations of Amyloid β-peptide (1-42) studied by molecular dynamics simulation
Yang, Cao
Li, Jinyu
Li, Yu
Zhu, Xiaolei
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2009, 895 (1-3): : 1 - 8
[35] Elevated plasma amyloid β-peptide 1-42 and onset of dementia in adults with Down syndrome
Schupf, N
Patel, B
Silverman, W
Zigman, WB
Zhong, N
Tycko, B
Mehta, PD
Mayeux, R
NEUROSCIENCE LETTERS, 2001, 301 (03) : 199 - 203
[36] Decreased serum amyloid β1-42 autoantibody levels in Alzheimer's disease, determined by a newly developed immuno-precipitation assay with radiolabeled amyloid β1-42 peptide
Brettschneider, S
Morgenthaler, NG
Teipel, SJ
Fischer-Schulz, C
Bürger, K
Dodel, R
Du, YS
Möller, HJ
Bergmann, A
Hampel, H
BIOLOGICAL PSYCHIATRY, 2005, 57 (07) : 813 - 816
[37] In vitro and in vivo oxidative stress associated with Alzheimer's amyloid β-peptide (1-42)
Yatin, SM
Varadarajan, S
Link, CD
Butterfield, DA
NEUROBIOLOGY OF AGING, 1999, 20 (03) : 325 - 330
[38] Solid-phase synthesis of homodimeric peptides: preparation of covalently-linked dimers of amyloid β peptide
Kok, W. Mei
Scanlon, Denis B.
Karas, John A.
Miles, Luke A.
Tew, Deborah J.
Parker, Michael W.
Barnham, Kevin J.
Hutton, Craig A.
CHEMICAL COMMUNICATIONS, 2009, (41) : 6228 - 6230
[39] Intracellular Ion Channel CLIC1: Involvement in Microglia-Mediated β-Amyloid Peptide(1-42) Neurotoxicity
Skaper, Stephen D.
Facci, Laura
Giusti, Pietro
NEUROCHEMICAL RESEARCH, 2013, 38 (09) : 1801 - 1808
[40] Inhibition of amyloid β1-42 peptide aggregation by newly designed cyclometallated palladium complexes
Saini, Rahul
Navale, Govinda R.
Singh, Sain
Singh, Haobam Kisan
Chauhan, Rahul
Agrawal, Sonia
Sarkar, Dhiman
Sarma, Manabendra
Ghosh, Kaushik
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2023, 248

← 1 2 3 4 5 →