Nα-Boc-Nδ-tosyl-Arg-OBt | 105916-77-6

• 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: Nα-Boc-Nδ-tosyl-Arg-OBt
• 英文别名: N^α-Boc-N^δ-tosyl-Arg-OBt；Boc-L-Arg(Tos)-OBt；Boc-Arg(Tos)-OBt
• CAS: 105916-77-6
• 化学式: C₂₄H₃₁N₇O₆S
• 分子量: 545.619
• InChiKey: VUUMMIAJJJWPRG-IBGZPJMESA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  177.39
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Nα-Boc-Nδ-tosyl-Arg-OBt 在 N-甲基吗啉 、 盐酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 84.0h， 生成 Boc-Ala-Arg(Tos)-Pro-Ala-Lys(Z)-OBzl
  参考文献：
  名称：

  Zhao, Ming; Peng, Shiqi, Advanced Synthesis and Catalysis, 1999, vol. 341, # 7, p. 668 - 676

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 Nα-Boc-Nδ-tosyl-Arg-OBt
  参考文献：
  名称：

  Novel nano-materials, RGD-tetrapeptide-modified 17β-amino-11α-hydroxyandrost-1,4-diene-3-one: synthesis, self-assembly based nano-images and in vivo anti-osteoporosis evaluation

  摘要：

  为了寻找具有抗骨质疏松活性且无副作用的新型纳米材料，通过结合抑制骨吸收活性的RGD多肽和具有抗骨质疏松活性的17β-氨基-11α-羟基雄甾-1,4-二烯-3-酮，构建了三种新型抗骨质疏松活性的两亲性分子，17β-(RGD-AA-酰胺)-11α-羟基雄甾-1,4-二烯-3-酮（5a：AA = Ser，5b：AA = Val，5c：AA = Phe）。在固态下，5a，5b和5c分别以直径为300 nm至14 μm的分散球体、直径为110 nm至19 μm的分散蛋和直径为238 nm至22 μm的珠子存在。在超纯水中，1.1 μM的5a，5b和5c分别形成直径为33至400 nm、16至278 nm和54至187 nm的纳米球体。在口服剂量为110 nmol kg-1时，5a至5c有效地抑制了小鼠的骨质疏松发展。与雌二醇相比，5a至5c不会导致小鼠子宫内膜增生和血栓形成。

  DOI：

  10.1039/c2jm13983a

文献信息

• Application of an Automated Synthesis Suite to Parallel Solution-Phase Peptide Synthesis.
  作者：Noritaka KURODA、Taeko HATTORI、Yoko FUJIOKA、David G. CORK、Chieko KITADA、Tohru SUGAWARA

  DOI：10.1248/cpb.49.1147

  日期：——

  An in-house developed automated synthesis suite was used to prepare a library of 72 tetrapeptide derivatives, the starting materials for pharmaceutically attractive pentapeptides, employing a convergent strategy. An initial set of 18 dipeptides were synthesized on a large-scale (100-1000 g) using automated synthesis workstations, and then 72 tetrapeptides were synthesized on a medium scale (5-10 g) using an automated system. Each di- or tetrapeptide was prepared in a single operating cycle using a modified methanesulfonic acid method, then a sub-library of 56 pentapeptides were synthesized in parallel, on a small-scale (100 mg-1 g) using a robotic workstation.

  使用一套自主研发的自动化合成系统，制备了72个四肽衍生物库，这些是用于合成具有药物吸引力的五肽的起始材料，采用了一种汇聚策略。首先，利用自动化合成工作站大规模（100-1000克）合成了18种二肽，然后使用自动化系统在中等规模（5-10克）合成了72种四肽。每个二肽或四肽均在单个操作周期中使用改良的甲磺酸方法制备，随后在小型规模（100毫克-1克）下利用机器人工作站并行合成了56种五肽的子库。
• Design and synthesis of highly potent and selective cyclic dynorphin A analogs. 2. New analogs
  作者：Andrew M. Kawasaki、Richard J. Knapp、Thomas H. Kramer、Amanda Walton、William S. Wire、Shinicki Hashimoto、Henry I. Yamamura、Frank Porreca、Thomas F. Burks、Victor J. Hruby

  DOI：10.1021/jm00058a012

  日期：1993.3

  We have designed and synthesized several cyclic disulfide-containing peptide analogs of dynorphin A (Dyn A) which are conformationally constrained in the putative ''address' segment of the opioid ligand. Several of these Dyn A analogs exhibit unexpected apparent selectivities for the kappa and mu opioid receptors(s) of the central vs peripheral nervous systems. Thus, incorporation of conformational constraint in the putative ''address'' segment of Dyn A analogs has resulted in the kappa/mu opioid receptor ligands [L-Pen5,Cys11]Dyn A1-11-NH2 (4), [Cys5,Cys10]Dyn A1-11-NH2 (5), [Cys5,Cys9]DynA1-11-NH2(6), and [Cys4,Cys9,Arg10]DynA1-11-NH2(7). All of these analogs possess high kappa and mu opioid receptor affinities for the central receptor (guinea pig brain), but effect only weak potency at peripheral kappa and mu opioid receptors (GPI). In fact cyclic dynorphin A analog 4 shows >19 000-fold differences between central kappa opioid affinity and potency in the guinea pig ileum (GPI). Additionally analog 4 is not an antagonist in the GPI, suggesting possible receptor differences between these sites. Substitution of Tyr1 by Phe1 in the cyclic 1-11 series gave the analog [Phe1,Cys5,Cys11]Dyn A1-11-NH2 (1) that was surprisingly potent in the guinea pig brain binding assay (IC50 = 15.1 nM) at the kappa receptor, but was inactive in the GPI and mouse vas deferens bioassays. D-Ala2 and TiC4 analogs of 1 had lower affinity at brain kappa receptors and had very weak potencies in the GPI and MVD bioassays. On the other hand, [Cys6,Cys10]DynA1-11-NH2 (8), [Cys8,D-Cys13]DynA1-13-NH2 (9), [D-CyS8,D-CyS12 ]DynA1-13-NH2 (10), and [D-Pro10,Cys5, Cys13]-Dyn Al-13-NH2 (11) were surprisingly potent in the GPI bioassay, though considerable apparent selectivity for central receptors is still retained. The apparent lack of correlation between the pharmacological profiles observed in smooth muscle and in the brain binding assays, particularly with 1 and 4, may suggest the existence of different subtypes of the kappa and mu opioid receptors in the brain and peripheral systems.
• Krchnak, Viktor; Vagner, Josef; Hirsch, Ivan, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11A, p. 2645 - 2653
  作者：Krchnak, Viktor、Vagner, Josef、Hirsch, Ivan

  DOI：——

  日期：——