Z-Asn-NH2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Z-Asn-NH2
• 英文别名: Benzyloxy-carbonyl-l-asparagine amide；benzyl N-[(2S)-1,4-diamino-1,4-dioxobutan-2-yl]carbamate
• 化学式: C₁₂H₁₅N₃O₄
• 分子量: 265.269
• InChiKey: NGQXBWKMPPALND-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Z-Asn-NH2 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以87%的产率得到Asn-NH2
  参考文献：
  名称：

  醇溶剂中二甲基硫代膦酰氯混合酸酐法合成肽

  摘要：

  受保护氨基酸的二甲基硫代膦酸混合酸酐的形成和偶联可以在醇溶剂中进行。通过该技术合成了直至七肽阶段的血管活性肠肽 (VIP) 的微溶保护 C 末端片段，并对其进行了充分表征。

  DOI：

  10.1246/bcsj.61.3653
• 作为产物：
  描述：

  (S)-3-n-cbz-氨基琥珀酰亚胺 在 ammonium hydroxide 作用下， 生成 Z-Asn-NH2
  参考文献：
  名称：

  Imides from Asparagine and Glutamine¹

  摘要：

  DOI：

  10.1021/ja01638a047

文献信息

• Peptide Synthesis in Alcohol Solvents by the Mixed Anhydride Method Using Dimethylphosphinothioyl Chloride
  作者：Masaaki Ueki、Takashi Saito、Jun Sasaya、Shigeru Ikeda、Hidekazu Oyamada

  DOI：10.1246/bcsj.61.3653

  日期：1988.10

  and coupling of the dimethylphosphinothioic mixed anhydrides of protected amino acids can be performed in alcohol solvents. Sparingly soluble protected C-terminal segments of vasoactive intestinal peptide (VIP) up to the heptapeptide stage were synthesized by this technique and fully characterized.

  受保护氨基酸的二甲基硫代膦酸混合酸酐的形成和偶联可以在醇溶剂中进行。通过该技术合成了直至七肽阶段的血管活性肠肽 (VIP) 的微溶保护 C 末端片段，并对其进行了充分表征。
• Enzymatic C-terminal amidation of amino acids and peptides
  作者：Timo Nuijens、Elena Piva、John A.W. Kruijtzer、Dirk T.S. Rijkers、Rob M.J. Liskamp、Peter J.L.M. Quaedflieg

  DOI：10.1016/j.tetlet.2012.05.039

  日期：2012.7

  enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic

  在本文中，我们描述了两种通用且高产的酶促方法，可将半保护的氨基酸和肽基C末端α-羧酸转化为它们相应的酰胺。在第一种方法中，分别使用脂肪酶南极假丝酵母脂肪酶-B（Cal-B），在第二种方法中，分别使用蛋白酶枯草杆菌蛋白酶A。我们发现，通过使用α-羧酸的铵盐代替单独的氨源，酶促酰胺化反应的进行速度大大加快，而没有副反应，并且使产物收率接近定量。
• Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission
  作者：Darshan Ranganathan、Narendra K. Vaish、Kavita Shah

  DOI：10.1021/ja00094a008

  日期：1994.7

  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.
• (2-Chloroethyl)nitrosourea congeners of amino acid amides
  作者：Tetsuo Suami、k Tsuguhiro Kato、Hiroaki Takino、Takashi Hisamatsu

  DOI：10.1021/jm00349a012

  日期：1982.7

  Fourteen (2-chloroethyl)nitrosourea congeners of L-amino acid amides have been synthesized as potential antineoplastic agents. Almost all the congeners tested were found to be highly active against experimental leukemia L1210 in mice. The chemical decomposition rates of the congeners were measured in a buffered solution (pH 7.4) at 37 degrees C. Acute toxicities of some of the congeners were determined for mice. The congener of sarcosinamide shows the longest half-life (T0.5 = 329.7 min) and the lowest toxicity, LD50 = 392.0 mg/kg (ip) and 426.6 mg/kg (iv), in this series.
• Liberek,B. et al., Roczniki Chemii, 1965, vol. 39, p. 369 - 374
  作者：Liberek,B. et al.

  DOI：——

  日期：——