Heating and microwave assisted SPPS of C-terminal acid peptides on trityl resin: the truth behind the yield

被引：18

作者：

Echalier, Cecile ^{[1
]}

Al-Halifa, Soultan ^{[2
]}

Kreiter, Aude ^{[1
]}

Enjalbal, Christine ^{[2
]}

Sanchez, Pierre ^{[2
]}

Ronga, Luisa ^{[1
]}

Puget, Karine ^{[1
]}

Verdie, Pascal ^{[2
]}

Amblard, Muriel ^{[2
]}

Martinez, Jean ^{[2
]}

Subra, Gilles ^{[2
]}

机构：

[1] Genepep Domaine Pins, F-34980 St Clement De Riviere, France

[2] UMR CNRS 5247, IBMM, F-34000 Montpellier, France

来源：

AMINO ACIDS | 2013年 / 45卷 / 06期

关键词：

Peptide synthesis; Microwave heating; Diketopiperazine; Fmoc/tBu strategy; 2-Chloro chlorotrityl resin; 2-CHLOROTRITYL CHLORIDE RESIN; ACYL ISOPEPTIDE METHOD; TRIPHENYLMETHYL ACETATE; ELEVATED-TEMPERATURES; AMINO-ACIDS; RACEMIZATION; CONDENSATION; CLEAVAGE;

D O I：

10.1007/s00726-013-1604-z

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Despite correct purity of crude peptides prepared on trityl resin by Fmoc/tBu microwave assisted solid phase peptide synthesis, surprisingly, lower yields than those expected were obtained while preparing C-terminal acid peptides. This could be explained by cyclization/cleavage through diketopiperazine formation during the second amino acid deprotection and third amino acid coupling. However, we provide here evidence that this is not the case and that this yield loss was due to high temperature promoted hydrolysis of the 2-chlorotrityl ester, yielding premature cleavage of the C-terminal acid peptides.

引用

页码：1395 / 1403

页数：9

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