A NOVEL MECHANISM FOR OXIDATIVE CLEAVAGE OF PROLYL PEPTIDES INDUCED BY THE HYDROXYL RADICAL
A NOVEL MECHANISM FOR OXIDATIVE CLEAVAGE OF PROLYL PEPTIDES INDUCED BY THE HYDROXYL RADICAL
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DOI：
10.1016/0006-291x(90)91463-3
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发表时间：
1990-05-31
影响因子：
3.1
通讯作者：
KAWAKISHI, S
中科院分区：
文献类型：
--
作者：
UCHIDA, K;KATO, Y;KAWAKISHI, S
研究了羟基自由基(.oh)引起的含脯氨酸多肽的氧化裂解机理。伴随着脯氨酸多肽的氧化，我们发现在氧化多肽的酸性水解物中形成了大量的γ-氨基丁酸(GABA)。GABA被认为是由2-吡咯烷酮化合物产生的，此外，它的产生还导致了这样的假设，即脯氨酸肽主要是在Pro残基上被.oh裂解，并伴随着Pro自身的氧化修饰。因此，为了证实这一预测，我们利用Pro类似物(Z-Pro)进行了Pro与.OH的反应，并分离出了主要产物2-吡咯烷酮类化合物。我们提出了·OH诱导2-吡咯烷酮化合物形成的新机制，这是首次在脯氨酸多肽的氧化裂解中建立的。
Mechanism for the oxidative cleavage of proline-containing peptides induced by the hydroxyl radical (.OH) has been studied. Accompanying the oxidation of prolyl peptides, we discovered the formation of significant amounts of .gamma.-aminobutyric acid (GABA) in the acid hydrolysates of the oxidized peptides. GABA was assumed to be derived from the 2-pyrrolidone compound and, in addition, its generation led to the assumption that prolyl peptides were mainly cleaved at the proline residues by .OH, accompanied by the oxidative modification of proline by itself. Hence, in order to confirm this prediction, we undertook the reaction of proline with .OH using proline analogue (Z-proline) and isolated the 2-pyrrolidone compound as the major product. We proposed a novel mechanism for formation of the 2-pyrrolidone compound induced by .OH, which has been established for the first time in the oxidative cleavage of prolyl peptides.