Synthesis of Peptide Cysteine Dimedone Using Fmoc‐Cys(Dmd)‐OH: Glutathione Cysteine Dimedone as a Probe in Investigating the Sulfenic Acid Mediated Oxidation of Glutathione,Helvetica Chimica Acta

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Synthesis of Peptide Cysteine Dimedone Using Fmoc‐Cys(Dmd)‐OH: Glutathione Cysteine Dimedone as a Probe in Investigating the Sulfenic Acid Mediated Oxidation of Glutathione
Helvetica Chimica Acta ( IF 1.5 ) Pub Date : 2020-05-29 , DOI: 10.1002/hlca.202000062
K. Kasi Amarnath Reddy ₁ , Smriti Moi ₁ , Ashwini Dolle ₁ , Basavaprabhu Hosamani ₁ , Kiran Krishnamurthy ₂ , Sunita Prakash ₃ , Srinivasarao Raghothama ₂ , Konkallu Hanumae Gowd ₁

Affiliation

Dimedone is the most widely used chemical probe for detection of cysteine sulfenic acid in peptides and proteins. The reaction of dimedone with cysteine sulfenic acid results in the formation of unique cysteine dimedone motif containing thioether bridge. Based on the structure of cysteine dimedone residue in polypeptide, a new building block of Fmoc‐Cys(Dmd)‐OH was developed for solid phase synthesis of peptide cysteine dimedone. Mass spectrometric sequencing of synthetic peptides have confirmed successful incorporation of cysteine dimedone in peptide chain using HBTU/HOBt as a coupling agent. The new method permits synthesis of peptides containing both cysteine thiol and cysteine dimedone in the same sequence which was difficult to achieve by conventional methods. The synthetic peptide of glutathione cysteine dimedone was used as a standard in probing the air‐mediated oxidation of thiol to disulfide form of glutathione. The co‐elution of standard peptide and reaction mixture of oxidation of glutathione in presence of dimedone using RP‐HPLC have confirmed the formation of glutathione cysteine sulfenic as an intermediate in the air‐mediated oxidation of glutathione. The synthetic peptides of cysteine dimedone may find application in the field of redox proteomics and generation of antibodies against modified cysteine residue.

中文翻译：

用Fmoc-Cys（Dmd）-OH合成肽半胱氨酸二甲酮：谷胱甘肽半胱氨酸二甲酮作为考察磺酸介导的谷胱甘肽氧化的探针

Dimedone是检测肽和蛋白质中半胱氨酸亚磺酸最广泛使用的化学探针。二甲酮与半胱氨酸亚磺酸的反应导致形成独特的含硫醚桥的半胱氨酸二甲酮基序。根据多肽中半胱氨酸二甲酮残基的结构，开发了一种新的Fmoc-Cys（Dmd）-OH构建基块，用于固相合成肽半胱氨酸二甲酮。合成肽的质谱测序已证实使用HBTU / HOBt作为偶联剂成功地将半胱氨酸二甲酮掺入肽链中。新方法允许以相同的序列合成同时包含半胱氨酸硫醇和半胱氨酸二甲酮的肽，这是常规方法难以实现的。谷胱甘肽半胱氨酸二甲酮的合成肽被用作探测空气介导的硫醇氧化成谷胱甘肽二硫键的标准。使用RP-HPLC共洗脱标准肽和谷胱甘肽在二甲酮存在下的氧化反应混合物，证实了谷胱甘肽半胱氨酸亚砜在空气介导的谷胱甘肽氧化中的形成。半胱氨酸二甲酮的合成肽可用于氧化还原蛋白质组学和产生针对修饰的半胱氨酸残基的抗体的领域。使用RP-HPLC共洗脱标准肽和谷胱甘肽在二甲酮存在下的氧化反应混合物，证实了谷胱甘肽半胱氨酸亚砜在空气介导的谷胱甘肽氧化中的形成。半胱氨酸二甲酮的合成肽可在氧化还原蛋白质组学和产生针对修饰的半胱氨酸残基的抗体的领域中找到应用。使用RP-HPLC共洗脱标准肽和谷胱甘肽在二甲酮存在下的氧化反应混合物，证实了谷胱甘肽半胱氨酸亚砜在空气介导的谷胱甘肽氧化中的形成。半胱氨酸二甲酮的合成肽可用于氧化还原蛋白质组学和产生针对修饰的半胱氨酸残基的抗体的领域。

更新日期：2020-05-29

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