Boc-L-Thr(Bn)-NHCH3 | 149639-95-2

• 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: Boc-L-Thr(Bn)-NHCH3
• 英文别名: Boc-L-Thr(OBn)-NHMe；Boc-Thr(OBn)-NHCH3；(2S,3R)-2-[(tert-butoxy)carbonylamino]-N-methyl-3-(phenylmethoxy)butanamide；tert-butyl N-[(2S,3R)-1-(methylamino)-1-oxo-3-phenylmethoxybutan-2-yl]carbamate
• CAS: 149639-95-2
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: PLNLBNCAUZAVTJ-OCCSQVGLSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  500.7±50.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-L-Thr(Bn)-NHCH3 在 palladium on activated charcoal 2,6-二甲基吡啶 、 硫酸 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 216.0h， 生成 4-((1S,2R)-2-Hydroxy-1-methylcarbamoyl-propylcarbamoyl)-butyric acid tert-butyl ester
  参考文献：
  名称：

  Bio-orthogonal Affinity Purification of Direct Kinase Substrates

  摘要：

  Protein phosphorylation is a major mechanism of post-translational protein modification used to control cellular signaling. A challenge in phosphoproteomics is to identify the direct substrates of each protein kinase. Herein, we describe a chemical strategy for delivery of a bio-orthogonal affinity tag to the substrates of an individual protein kinase. The kinase of interest is engineered to transfer a phosphorothioate moiety to phosphoacceptor hydroxyl groups on direct substrates. In a second nonenzymatic step, the introduced phosphorothioate is alkylated with p-nitrobenzylmesylate (PNBM). Antibodies directed against the alkylated phosphorothioate epitope recognize these labeled substrates, but not alkylation products of other cellular nucleophiles. This strategy is demonstrated with Cdk1/cyclinB substrates using ELISA, western blotting, and immunoprecipitation in the context of whole cell lysates.

  DOI：

  10.1021/ja050727t
• 作为产物：
  描述：

  N-Boc-O-苄基-L-苏氨酸 以 甲醇 、 二氯甲烷 为溶剂， 生成 Boc-L-Thr(Bn)-NHCH3
  参考文献：
  名称：

  Total Synthesis of (-)-Thiangazole, a Naturally-Occurring HIV-1 Inhibitor

  摘要：

  (-)-硫唑烷（1），一种天然的HIV-1抑制剂，已通过全合成方法制备成功。

  DOI：

  10.1021/jo00096a012

文献信息

• Thio Acid/Azide Amidation:  An Improved Route to <i>N</i>-Acyl Sulfonamides
  作者：Kristin N. Barlett、Robert V. Kolakowski、Sreenivas Katukojvala、Lawrence J. Williams

  DOI：10.1021/ol052671d

  日期：2006.3.2

  A one-pot procedure for the conversion of carboxylic acids to N-acyl sulfonamides, via thio acid/azide amidation, is presented. The method is compatible with acid- and base-sensitive amino acid protection. N-Acyl sulfonamide synthesis on solid support, peptide thio acid/sulfonazide coupling, and N-alkyl amide synthesis via selective cleavage of sulfonyl from an N-alkyl-N-acyl sulfonamide are also reported

  提出了一种一锅法，用于通过硫代酸/叠氮化物酰胺化将羧酸转化为N-酰基磺酰胺。该方法与对酸和碱敏感的氨基酸保护兼容。还报道了在固体载体上合成N-酰基磺酰胺，肽硫酸/磺叠氮化物偶联以及通过从N-烷基-N-酰基磺酰胺选择性裂解磺酰基而合成的N-烷基酰胺。
• Total synthesis of thiangazole
  作者：Kenichi Akaji、Yoshiaki Kiso

  DOI：10.1016/s0040-4020(99)00604-3

  日期：1999.8

  A method for total synthesis of thiangazole (1), a tris-thiazoline-oxazole metabolite, is described. The key intermediate 9, a linear tetrapeptide amide composed of three S-benzyl-2-methylcysteine residues and a O-benzyl-threonine amide, was synthesized in 4 steps using 2-chloro-1,3-dimethyl-imidazolidium hexafluorophosphate(CIP)-mediated activation. The successive thiazoline/oxazole rings were constructed

  描述了全合成噻唑（1），一种三噻唑啉-恶唑代谢物的方法。使用2-氯-1,3-二甲基-咪唑六氟磷酸盐（CIP）分四步合成了关键中间体9，即由三个S-苄基-2-甲基半胱氨酸残基和一个O-苄基苏氨酸酰胺组成的线性四肽酰胺介导的激活。连续的噻唑啉/恶唑环是通过TiCl 4介导的环脱水反应，然后无困难地通过酸催化的Robinson-Gabriel反应构建的。
• Effect of β-O-Glucosylation onL-Ser andL-Thr Diamides: A Bias toward α-Helical Conformations
  作者：Francisco Corzana、Jesús H. Busto、Søren B. Engelsen、Jesús Jiménez-Barbero、Juan L. Asensio、Jesús M. Peregrina、A. Avenoza

  DOI：10.1002/chem.200600128

  日期：2006.10.16

  Beta-D-O-glucosylation produces a remarkable effect on the peptide backbone of the model peptides derived from serine and threonine. Consequently, this type of glycosylation is responsible for the experimentally observed shift from extended conformations (model peptides) towards the folded conformations (model glycopeptides). The conclusion has been solidly assessed by a combined NMR/MD protocol. Interestingly

  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。
• Inhibitors of anthrax lethal factor
  申请人：Rideout Darryl

  公开号：US20070197577A1

  公开（公告）日：2007-08-23

  Methods, compounds and compositions for preventing and treating anthrax infections by inhibiting Anthrax Lethal Factor (LF) activity.

  通过抑制炭疽病致命因子（LF）活性，预防和治疗炭疽感染的方法，化合物和组合物。
• Synthesis and structure of cyclic phosphopeptides containing a phosphodiester linkage
  作者：Anita H. van Oijen、Stefan Behrens、Dale F. Mierke、Horst Kessler、Jacques H. van Boom、Rob M. J. Liskamp

  DOI：10.1021/jo00066a026

  日期：1993.7

  The synthesis of three cyclic phosphopeptides, which contain a phosphodiester linkage, is described. Starting from either Boc-L-Ser(OBn)-OH or BOC-L-Thr(OBn)-OH, three precursors for the macro-cyclization by phosphitylation were prepared. After phosphitylation, using 4-chlorobenzyl bis(N,N-diisopropylamino)phosphinite or 4-chlorobenzyl dichlorophosphinite, subsequent oxidation and hydrogenolysis the cyclic phosphopeptides 18-20 were obtained. The solution conformation of cyclic phosphopeptide 18 was studied by NMR spectroscopy and restrained molecular dynamics calculations.