N-Acetyl-L-serin-methylamid | 6367-12-0

• 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: N-Acetyl-L-serin-methylamid
• 英文别名: (2S)-2-acetamido-3-hydroxy-N-methylpropanamide
• CAS: 6367-12-0
• 化学式: C₆H₁₂N₂O₃
• 分子量: 160.173
• InChiKey: WAZDXKZPWRIFLK-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Acetyl-L-serin-methylamid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以82%的产率得到N-acetyldehydroalanine N'-methylamide
  参考文献：
  名称：

  Effects of dehydroalanine on peptide conformations

  摘要：

  The conformational preferences of dehydroalanine were examined through a combined approach of X-ray diffraction, NMR spectroscopy, and molecular modeling. Monte Carlo simulated annealing was used in conjunction with X-ray diffraction data and semiempirical quantum mechanical calculations to determine appropriate parameters for modeling dehydroalanine with the DISCOVER consistent valence force field. The two molecules in the asymmetric unit of N-acetyldehydroalanine N'-methylamide were simulated in the crystalline environment using these optimized parameters. The rms deviations between simulation and experimental data for heavy atom bond lengths, bond angles, and torsions were 0.021 angstrom, 1.9-degrees, and 8.7-degrees, respectively. The dehydroalanine-containing ring A fragment of nisin and two analogs with either L- or D-alanine substituted for dehydroalanine were synthesized and examined by NMR spectroscopy. Using distance geometry followed by conformational energy minimization with our optimized parameters, families of conformations were determined for each molecule which satisfied the observed backbone NOE, J(alpha-N) coupling constants, and temperature coefficients. Dehydroalanine adopted a roughly planar conformation, with trans orientations for the phi and psi-torsions, and induced an inverse gamma-turn in the preceding residue. Similar effects have been observed for linear, dehydroalanine-containing peptides in solution and as crystals, suggesting that dehydroalanine exerts a powerful conformational influence independent of other constraints. The conformational preferences of the L- and D-Ala ring A analogs differed substantially from each other and from the ring A fragment.

  DOI：

  10.1021/ja00040a024
• 作为产物：
  描述：

  N-acetyl-O-benzylserine methylamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以95%的产率得到N-Acetyl-L-serin-methylamid
  参考文献：
  名称：

  β-O-葡萄糖基化对L-Ser和L-Thr二酰胺的影响：偏向α-螺旋构象。

  摘要：

  β-DO-葡萄糖基化对衍生自丝氨酸和苏氨酸的模型肽的肽主链产生显着影响。因此，这种类型的糖基化负责实验上观察到的从延伸构象（模型肽）向折叠构象（模型糖肽）的转变。该结论已经通过NMR / MD组合方案进行了可靠的评估。有趣的是，糖肽的MD（分子动力学）结果表明糖和肽部分之间存在水桥分子，这可以解释水溶液中折叠构象异构体的稳定性。

  DOI：

  10.1002/chem.200600128

文献信息

• Synthesis of Casein-Related Peptides and Phosphopeptides. IV. Phosphorotriester and 'Phosphite-Triester' Phosphorylation of Protected Serine-Containing Peptides
  作者：JW Perich、RB Johns

  DOI：10.1071/ch9901609

  日期：——

  The phosphorylation of Ac-Ser- NHMe or Ac- Gly-Ser-Gly-NHMe with diphenyl phosphorochloridate /pyridine gave diphenyl hydrogen phosphate in high yield instead of the expected-Ser(PO3Ph2)-peptide. A 31P n.m.r . spectroscopy study of the phosphorylation reaction established that, with the use of diphenyl phosphorochloridate in pyridine, the intermediate diphenyl phosphoro-N-pyridinium chloride was the active phosphorylation species and that phosphorylation of the hydroxy group of Ac-Ser- NHMe or Ac- Gly-Ser-Gly-NHMe was followed by rapid dephosphorylation of the O-( diphenylphosphono ) seryl residue. While diethyl phosphorochloridate /pyridine phosphorylation of Ac-Ser- NHMe also did not give Ac-Ser(PO3Et2)- NHMe, both the two-step ( i ) diethyl phosphorochloridite /pyridine, (ii) iodine/water and the two-step (i) diethyl N,N-diethylphosphoramidite/1H-tetrazole, (ii) iodine/water 'phosphite-triester' phosphorylation of Ac-Ser- NHMe gave Ac- Ser(PO3Et2)- NHMe in high yield.

  用二苯基磷酰氯/吡啶对 Ac-Ser- NHMe 或 Ac- Gly-Ser-Gly-NHMe 进行磷酸化反应，可获得高产率的磷酸二苯基氢，而不是预期的er(PO3Ph2)肽。对磷酸化反应的 31P n.m.r .光谱研究表明，在吡啶中使用二苯基磷酰氯时，中间体二苯基磷-N-吡啶氯化物是活跃的磷酸化物种，Ac-Ser- NHMe 或 Ac- Gly-Ser-Gly-NHMe 的羟基磷酸化后，O-( 二苯基磷) 丝氨酸残基迅速去磷酸化。虽然二乙基氯膦酸盐/吡啶对 Ac-Ser- NHMe 的磷酸化也不会产生 Ac-Ser(PO3Et2)-NHMe，但两步法（i）二乙基氯膦酸盐/吡啶、(ii) 碘/水和两步法 (i) N,N-二乙基亚磷酰胺二乙酯/1H-四氮唑，(ii) 碘/水 "亚磷酸三酯 "磷酸化 Ac-Ser- NHMe，都能高产率地得到 Ac-Ser(PO3Et2)-NHMe。
• Synthesis of Casein-Related Peptides and Phosphopeptides. VI. The Efficient Global 'Phosphite-Triester' Phosphorylation of Multiple-Serine-Containing Peptides by Using Dibenzyl N,N-Diethylphosphoramidite
  作者：JW Perich、RB Johns

  DOI：10.1071/ch9901633

  日期：——

  The peptide Ac-Ser(P)- NHMe and the multiple-Ser(P)-containing peptides Ac-Ser(P)-Ser(P)- NHMe and Ac-Ser(P)-Ser(P)-Ser(P)- NHMe were prepared in good yield by a global phosphorylation approach which employed benzyl phosphate protection. The three serine-containing peptides were phosphorylated by the use of dibenzyl N,N-diethylphosphoramidite/1H-tetrazole followed by in situ oxidation of the resultant dibenzyl phosphite-triesters with m- chloroperoxybenzoic acid. The protected Ser(PO3Bzl2)-containing peptides were purified by C18 reverse-phase silica flash column chromatography and the benzyl phosphate groups were cleaved from the protected Ser(PO3Bzl2) peptides by palladium- catalysed hydrogenolysis.

  采用磷酸苄基酯保护的全局磷酸化方法制备了多肽 Ac-Ser(P)-NHMe，以及含有多个丝氨酸（P）的多肽 Ac-Ser(P)-Ser(P)-NHMe 和 Ac-Ser(P)-Ser(P)-Ser(P)-NHMe，并取得了良好的收率。先用 N,N-二乙基亚磷酰胺二苄酯/1H-四氮唑对这三种含丝氨酸的肽进行磷酸化，然后用间氯过氧苯甲酸对得到的亚磷酸二苄酯进行原位氧化。受保护的含 Ser(PO3Bzl2) 多肽经 C18 反相硅胶闪速柱层析纯化，受保护的 Ser(PO3Bzl2) 多肽中的磷酸苄基在钯催化下氢解。
• Tyrosine Bioconjugation through Aqueous Ene-Like Reactions
  申请人：Barbas, III Carlos F.

  公开号：US20120289682A1

  公开（公告）日：2012-11-15

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an Ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. This reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  报道了一种新型多功能环状二氮基二羧酰胺类化合物，通过Ene反应与苯酚和酪氨酸的苯基侧链高效选择性反应。这种温和的水相酪氨酸连接反应适用于广泛的pH范围，并扩展了小分子、肽和蛋白质修饰的水相化学反应库。该酪氨酸连接反应可与缓冲水溶液中的天然酶和抗体标记兼容。该反应提供了一种新的双特异性抗体合成方法。该反应将在肽和蛋白质化学以及含酚化合物的化学中发挥广泛的实用价值。
• COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER
  申请人：Beckman Barbara S.

  公开号：US20120027844A1

  公开（公告）日：2012-02-02

  Compounds and their syntheses are disclosed herein. Compositions and pharmaceutical compositions comprising a compound are also described, and include compositions also comprising liposomes. Methods for the treatment of cancer in animals comprising administering a compound or a composition comprising a compound are also described.

  本文披露了化合物及其合成方法。还描述了包含化合物的组合物和药物组合物，其中包括还包含脂质体的组合物。还描述了用于治疗动物癌症的方法，包括给动物施用化合物或包含化合物的组合物。
• Reaktivität von Aminosäure-Seitenkettengruppen, II. N-Acetyl-methylamide von Threonin und Hydroxyprolin
  作者：HELMUT ZAHN、GERHARD REINERT

  DOI：10.1515/bchm2.1968.349.1.608

  日期：1968.1