Bz-Ala-NH2 | 67711-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Bz-Ala-NH2
• 英文别名: Benzoylalaninamid；N-[(2S)-1-amino-1-oxopropan-2-yl]benzamide
• CAS: 67711-04-0
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: ZWDNWUISPPRMSS-ZETCQYMHSA-N

物化性质

• 熔点：
  235-240 °C
• 沸点：
  476.4±28.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Bz-Ala-Thr-OMe 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 0.5h， 以65%的产率得到Bz-Ala-NH2
  参考文献：
  名称：

  Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission

  摘要：

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.

  DOI：

  10.1021/ja00094a008

文献信息

• Peptide backbone cleavage by <i>α</i> -amidation is enhanced at methionine residues
  作者：Michael Hellwig、Katja Löbmann、Tom Orywol

  DOI：10.1002/psc.2713

  日期：2015.1

  Cleavage reactions at backbone loci are one of the consequences of oxidation of proteins and peptides. During α‐amidation, the Cα–N bond in the backbone is cleaved under formation of an N‐terminal peptide amide and a C‐terminal keto acyl peptide. On the basis of earlier works, a facilitation of α‐amidation by the thioether group of adjacent methionine side chains was proposed. This reaction was characterized

  骨架位点的裂解反应是蛋白质和肽氧化的后果之一。在α酰胺化过程中，主链中的Cα – N键在N末端肽酰胺和C末端酮酰基肽的形成下被裂解。在早期工作的基础上，对α的促进提议通过相邻甲硫氨酸侧链的硫醚基团酰胺化。通过使用苯甲酰基甲硫氨酸和苯甲酰基丙氨酰甲硫氨酸作为肽模型来表征该反应。在不同的碳水化合物化合物（还原糖，Amadori产物和还原酮）存在下，于室温温育48小时，研究了苯甲酰化氨基酸（苯甲酰基蛋氨酸，苯甲酰基丙氨酸和苯甲酰基蛋氨酸亚砜）分解为苯甲酰胺。在醋酸盐缓冲溶液（pH 6.0）中为80°C。在所有糖和所有苯甲酰化物质的存在下，形成了少量的苯甲酰胺（0.3–1.5 mol％）。然而，当苯甲酰蛋氨酸在还原酮和Amadori化合物（3.5–4.2 mol％）存在下孵育时，苯甲酰胺的形成会大大增强。发现该反应是分子内的，因为α类似的4- methylbenzoylated氨基酸的-amida
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  DOI：10.1039/jr9610003394

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  作者：D. B. Henriksen、K. Breddam、J. Moeller、O. Buchardt

  DOI：10.1021/ja00031a049

  日期：1992.2
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