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 49 条

[11]

El-Agnaf OMA, 2000, PROTEIN PEPTIDE LETT, V7, P1

[12] Synthesis, aggregation, and neurotoxicity of the Alzheimer's Aβ1-42 amyloid peptide and its isoaspartyl isomers [J].

Fukuda, H ;

Shimizu, T ;

Nakajima, M ;

Mori, H ;

Shirasawa, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :953-956

[13] Solid-Phase Peptide Synthesis in Water Using Microwave-Assisted Heating [J].

Galanis, Athanassios S. ;

Albericio, Fernando ;

Grotli, Morten .

ORGANIC LETTERS, 2009, 11 (20) :4488-4491

[14] ChemMatrix, a poly(ethylene glycol)-based support for the solid-phase synthesis of complex peptides [J].

García-Martín, F ;

Quintanar-Audelo, M ;

García-Ramos, Y ;

Cruz, LJ ;

Gravel, C ;

Furic, R ;

Côté, S ;

Tulla-Puche, J ;

Albericio, F .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (02) :213-220

[15] ALZHEIMERS-DISEASE - INITIAL REPORT OF THE PURIFICATION AND CHARACTERIZATION OF A NOVEL CEREBROVASCULAR AMYLOID PROTEIN [J].

GLENNER, GG ;

WONG, CW .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 120 (03) :885-890

[16] Expedient synthesis and design strategies for new peptoid construction [J].

Gorske, BC ;

Jewell, SA ;

Guerard, EJ ;

Blackwell, HE .

ORGANIC LETTERS, 2005, 7 (08) :1521-1524

[17] Pseudo-prolines (ΨPro):: direct insertion of ΨPro systems into cysteine containing peptides [J].

Guichou, JF ;

Patiny, L ;

Mutter, M .

TETRAHEDRON LETTERS, 2002, 43 (24) :4389-4390

[18] Search for optimal coupling reagent in multiple peptide synthesizer [J].

Hachmann, J ;

Lebl, M .

BIOPOLYMERS, 2006, 84 (03) :340-347

[19] Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry [J].

Herrero, M. Antonia ;

Kremsner, Jennifer M. ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :36-47

[20] Structure of β-amyloid fibrils and its relevance to their neurotoxicity:: Implications for the pathogenesis of Alzheimer's disease [J].

Irie, K ;

Murakami, K ;

Masuda, Y ;

Morimoto, A ;

Ohigashi, H ;

Ohashi, R ;

Takegoshi, K ;

Nagao, M ;

Shimizu, T ;

Shirasawa, T .

JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 2005, 99 (05) :437-447

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