N-芴甲氧羰基-甲苯磺酰基-精氨酸 | 139090-50-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 精氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-芴甲氧羰基-甲苯磺酰基-精氨酸
• 中文别名: N-芴甲氧羰基-N'-甲苯磺酰基-L-精氨酸；FMOC-NW-(4-甲基磺酰)-L-精氨酸；Nα-Fmoc-Nω-甲苯磺酰基-L-精氨酸；NΑ-(9-芴甲氧羰基)-NΩ-甲苯磺酰基-L-精氨酸；NAlpha-[(9H-芴-9-基甲氧基)羰基]-Nω-甲苯磺酰基-L-精氨酸；Nα-FMOC-Nω-TOSYL-L-精氨酸；FMOC-对甲苯磺酰-精氨酸；Nα-芴甲氧羰基-Nω-甲苯磺酰基-L-精氨酸；FMOC-NΩ-(4-甲基磺酰)-L-精氨酸；Nα-[(9H-芴-9-基甲氧基)羰基]-Nω-甲苯磺酰基-L-精氨酸；Fmoc-Arg(tos)-OH
• 英文名称: N_α-FMOC-N_ω-L-tosylarginine
• 英文别名: Fmoc-Arg(Tos)-OH；Fmoc-Arg-(Tos)；Fmoc-Arg(Tos)；Fmoc-Arg(Ts)-OH；(2S)-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
• CAS: 139090-50-9；83792-47-6
• 化学式: C₂₈H₃₀N₄O₆S
• 分子量: 550.635
• InChiKey: JRRARHJPRLAGNT-VWLOTQADSA-N

物化性质

• 熔点：
  ~80 °C (dec.)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  溶于水或1%醋酸

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-甲苯磺酰基-精氨酸 在 草酰氯 、 氨 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.55h， 生成 N^α-FMOC-N^G-L-tosylargininecarboxamide
  参考文献：
  名称：

  The discovery, characterization and crystallographically determined binding mode of an FMOC-containing inhibitor of HIV-1 protease

  摘要：

  A pharmacophore derived from the structure of the dithiolane derivative of haloperidol bound in the active site of the HIV-1 protease (HIV-1 PR) has been used to search a three-dimensional database for new inhibitory frameworks. This search identified an FMOC-protected N-tosyl arginine as a lead candidate. A derivative in which the arginine carboxyl has been converted to an amide has been crystallized with HIV-1 PR and the structure has been determined to a resolution of 2.5 Angstrom with a final R-factor of 18.5%. The inhibitor binds in an extended conformation that results in occupancy of the S2, S1', and S3' subsites of the active site. Initial structure-activity studies indicate that: (1) the FMOC fluorenyl moiety interacts closely with active site residues and is important for binding; (2) the N-G-tosyl group is necessary to suppress protonation of the arginine guanidinyl terminus; and (3) the arginine carboxamide function is involved in interactions with the water coordinated to the catalytic aspartyl groups. FMOC-protected arginine derivatives, which appear to be relatively specific and nontoxic, offer promise for the development of useful HIV-1 protease inhibitors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00078-3

文献信息

• Orally Active Peptidic Bradykinin B1 Receptor Antagonists Engineered from a Cyclotide Scaffold for Inflammatory Pain Treatment
  作者：Clarence T. T. Wong、Dewi K. Rowlands、Chi-Hang Wong、Theodore W. C. Lo、Giang K. T. Nguyen、Hoi-Yeung Li、James P. Tam

  DOI：10.1002/anie.201200984

  日期：2012.6.4

  Edible: By grafting natural peptide antagonists onto the cyclotide kalata B1, orally active peptides were engineered, which are potentially useful therapeutics for the treatment of inflammatory pain. For example, the entire loop 6 of kalata B1 was replaced with the peptidic bradykinin B1 receptor antagonist DALK (red in scheme) to obtain the cyclic bradykinin antagonist ckb‐kal.

  食用：通过将天然肽拮抗剂移植到环肽kalata B1上，可设计出口服活性肽，这对于治疗炎性疼痛可能是有用的疗法。例如，用肽缓激肽B 1 受体拮抗剂DALK（方案中为红色）代替了卡拉塔B1的整个环6，以获得环状缓激肽拮抗剂ckb‐kal。
• Cu-Catalyzed Asymmetric Allylic Alkylations of Aromatic and Aliphatic Phosphates with Alkylzinc Reagents. An Effective Method for Enantioselective Synthesis of Tertiary and Quaternary Carbons
  作者：Monica A. Kacprzynski、Amir H. Hoveyda

  DOI：10.1021/ja0478779

  日期：2004.9.1

  Efficient enantioselective Cu-catalyzed allylic alkylations of aromatic and aliphatic allylic phosphates bearing di- and trisubstituted olefins are disclosed. Enantioselective C-C bond forming reactions are promoted in the presence of 10 mol % readily available chiral amino acid-based ligand (5 steps, 40% overall yield synthesis) and 5 mol % (CuOTf)2 x C6H6. Reactions deliver tertiary and quaternary stereogenic

  公开了带有二和三取代烯烃的芳族和脂族烯丙基磷酸酯的有效对映选择性Cu催化的烯丙基烷基化。在 10 mol% 容易获得的手性氨基酸基配体（5 步，40% 总产率合成）和 5 mol% (CuOTf)2 x C6H6 存在下，对映选择性 CC 键形成反应得到促进。反应区域选择性地以 78-96% ee 传递叔和四元立体碳中心。提供了有关配体结构变化对烷基化过程的效率和对映选择性的影响的数据，以及机械工作模型。建议的模型涉及手性 Cu 络合物的双重作用：Cu(I) 中心与烯烃的结合是通过配体羰基之间的两点结合来促进的
• A Practical Large-Scale Synthesis of Cyclic RGD Pentapeptides Suitable for Further Functionalization through ‘Click' Chemistry
  作者：Andreas Kirschning、Jiří Paleček、Gerald Dräger

  DOI：10.1055/s-0030-1258396

  日期：2011.2

  A multigram batch of the cyclo[Arg-Gly-Asp-d-Phe-Lys] and its N-ε-azido derivative was accomplished via solution-phase synthesis using an epimerization-free fragment condensation. The C-terminus of d-Phe was protected as its tert-butyl ester. Fmoc (Arg, Gly, Asp, d-Phe) and Boc (Lys) groups were used to protect all N-α-termini. The Ts and NO2 groups, respectively were chosen to protect the guanidine

  阿多克一批的环[精氨酸-甘氨酸- Asp-的d -Phe赖氨酸]及其Ñ -ε叠氮基衍生物，使用无差向异构化，片段缩合经由溶液相合成来完成。d- Phe的C末端被保护为叔丁基酯。Fmoc（Arg，Gly，Asp，d -Phe）和Boc（Lys）基团用于保护所有N -α-末端。分别选择Ts和NO 2基团来保护胍基。大环化步骤（在d -Phe和l之间-Lys）在TBTU / HOBt或DPPA缩合条件下进行。最后，通过重氮转移反应将赖氨酸残基的ε-氨基选择性地转化为叠氮基。 RGD肽-溶液相合成-氨基酸-环化-重氮化合物
• Convergent solid phase peptide synthesis. I. Synthesis of protected segments on a hydroxymethylphenyloxymethyl resin using the base labile FMOC α-amine protection. Model synthesis of LHRH.
  作者：E. Pedroso、A. Grandas、M.A. Saralegui、E. Giralt、C. Granier、J. van Rietschoten

  DOI：10.1016/0040-4020(82)85102-8

  日期：1982.1

  solid phase peptide synthesis has been applied to yield LHRH. The segments 1–6 and 7–10 of LHRH were synthesized on a hydroxymethylphenyloxymethyl resin using the base labile Fmoc protecting group on the α-amines. The side chains were protected by HF labile groups. Purification of the segments was performed on Sephadex LH-20 columns and by HPLC on Silica Gel 60 columns. The two segments were then assembled

  收敛固相肽合成已用于产生LHRH。LHRH的1–6和7–10片段是使用α-胺上的碱不稳定Fmoc保护基在羟甲基苯氧基甲基树脂上合成的。侧链受到H​​F不稳定基团的保护。片段的纯化在Sephadex LH-20柱上进行，并且通过HPLC在硅胶60柱上进行。然后将两个片段组装在α-氨基苄基树脂上以产生LHRH的完整序列。经Sephadex G-15和羧甲基纤维素CM-52进行HF处理并标准纯化后，获得所需的LHRH。通过相同的策略在咔唑基氧基甲基苯基氧基甲基树脂上合成链段显示出意想不到的困难。
• Total synthesis of marinostatin, a serine protease inhibitor isolated from the marine bacterium Pseudoallteromonas sagamiensis
  作者：Misako Taichi、Toshimasa Yamazaki、Terutoshi Kimura、Yuji Nishiuchi

  DOI：10.1016/j.tetlet.2009.02.213

  日期：2009.5

  Marinostatin (MST) (1) isolated from a marine organism is a serine protease inhibitor consisting of 12 amino acids with two internal ester linkages that are formed between the β-hydroxyl and β-carboxyl groups, Thr3-Asp9 and Ser8-Asp11. We synthesized MST by a regioselective esterification procedure employing two sets of orthogonally removable protecting groups at the side-chains of Asp and Ser/Thr

  从海洋生物中分离出的Marinostatin（MST）（1）是一种丝氨酸蛋白酶抑制剂，由12个氨基酸组成，带有在β-羟基和β-羧基，Thr 3 -Asp 9和Ser 8-之间形成的两个内部酯键。 Asp 11。我们通过区域选择性酯化方法合成了MST，该方法在Asp和Ser / Thr的侧链上使用了两组正交可移动的保护基。我们优化了酯化条件，以优先形成分子内酯键，而在Asp 9和Asp 11处没有任何明显的天冬酰胺（Asi）形成。合成MST对枯草杆菌蛋白酶（Ki，0.6 nM）与天然MST的报告值（1.5 nM）相当。