Nalpha-BOC-Nepsilon-CBZ-L-赖氨酸 DCHA | 16948-04-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Nalpha-BOC-Nepsilon-CBZ-L-赖氨酸 DCHA
• 中文别名: Nalpha-BOC-Nepsilon-CBZ-L-赖氨酸DCHA；Α-叔丁氧羰酰基氨基己酸苄基碳酰-L-赖氨酸二环己基胺；N6-苄氧羰基-N2-叔丁氧羰基-L-赖氨酸二环己胺盐
• 英文名称: N^α-tert-butyloxycarbonyl-N^ε-benzyloxycarbonyllysine dicyclohexylammonium salt
• 英文别名: Boc-Lys(Z)-OH dicyclohexylammonium salt；Boc-Lys(Cbz)-OH*DCHA；Boc-Lys(Z)-OH DCHA；Boc-Lys(Z)-OH*DCHA；Boc-Lys(Z) DCHA；Boc-Lys(Z)*DCHA；N-cyclohexylcyclohexanamine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 16948-04-2
• 化学式: C₁₂H₂₃N*C₁₉H₂₈N₂O₆
• 分子量: 561.762
• InChiKey: BQERJWRZLXZNIO-RSAXXLAASA-N

物化性质

• 熔点：
  114-116 °C

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29224985
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C

制备方法与用途

Boc-Lys(Z)-OH(DCHA)参与合成胸腺肽β4、βg和β6片段，还能增强狼疮性肾炎模型中E玫瑰花结的形成能力。此外，Boc-Lys(Z)-OH(DCHA)也用于合成Boc-Lys-OCH3，并作为肽基凝血酶抑制剂生产的试剂。

反应信息

• 作为反应物：
  描述：

  Nalpha-BOC-Nepsilon-CBZ-L-赖氨酸 DCHA 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 一水合肼 、 苯甲醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.67h， 生成 pyroglutamyl-alanyl-lysyl-seryl-glutaminyl-glycyl-glycyl-seryl-asparagine
  参考文献：
  名称：

  Effects of two synthetic serum thymic factor analogues and four thymic factor fragments on the low E-rosette forming cells in patients with chronic renal failure.

  摘要：

  通过溶液法合成了两种新型的血清胸腺因子(STF)类似物[Dab3]-STF和[Asn5, Gln9]-STF，以及四种胸腺因子片段H-Lys-Ser-Gln-OH、H-Lys-Ser-Gln-Gly-OH、H-Lys-Ser-Gln-Gly-OH和H-Lys-Ser-Gln-Gly-Gly-Ser-OH，并测试了它们对慢性肾衰竭患者低E玫瑰花结形成细胞的影响。类似物[Dab3]-STF和三种片段H-Lys-Ser-Gln-Gly-OH、H-Lys-Ser-Gln-Gly-Gly-OH和H-Lys-Ser-Gln-Gly-Gly-Ser-OH在体外与患者血液孵育时增加了E玫瑰花结形成能力，而[Asn5, Gln9]-STF和三肽H-Lys-Ser-Gln-OH则没有效果。

  DOI：

  10.1248/cpb.30.4448

文献信息

• Synthesis of the revised amino acid sequence of thymopoietin II and examination of its immunological effect on the impaired T-lymphocyte transformation of a uremic patient with pneumonia.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.35.2016

  日期：——

  The nonatetracontapeptide corresponding to the revised amino acid sequence of thymopoietin II was synthesized by assembling ten peptide fragments in solution followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole (molar ratio, 1 : 1) in trifluoroacetic acid in the presence of dimethylselenide and m-cresol. The synthetic nonatetracontapeptide was tested for effect on impaired T-lymphocyte transformation by phytohemagglutinin (PHA) in a uremic patient with pneumonia. The synthetic peptide was found to have restoring activity on the impaired PHA stimulation of T-lymphocytes; the minimum effective concentration was 1 μg/ml.

  通过溶液中组装十个肽片段，随后在二甲亚砜和间甲酚的存在下，用1 M三氟甲磺酸-硫代茴香醚（摩尔比1:1）在三氟乙酸中脱保护，合成了对应于胸腺生成素II修正氨基酸序列的非四十肽。对一名患有肺炎的尿毒症患者的受损T淋巴细胞由植物凝集素（PHA）诱导的转化作用进行了测试。发现合成肽具有恢复受损PHA刺激T淋巴细胞活性的能力；最小有效浓度为1 μg/ml。
• Synthesis of the octadecapeptide corresponding to positions 32 to 49 of the revised amino acid sequence of thymopoietin II and its effect on low E-rosette forming cells of an aged patient with chronic renal failure.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.30.3271

  日期：——

  The octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH, corresponding to positions 32 to 49 of the revised amino acid sequence of bovine thymopoietin II was synthesized by the azide condensation of three fragments, (32-36), (37-41) and (42-49), followed by deprotection with hydrogen fluoride in the presence of anisole-thioanisole-o-cresol. The in vitro addition of the synthetic thymopoietin II (32-49) significantly restored the low E-rosette forming capacity of cells from an aged patient with chronic renal failure to normal levels. The in vitro effect of [Gln38, Thr43, Val47]-thymopoietin II (32-49) on the low E-rosette forming capacity of cells from the aged patient with chronic renal failure was also compared with that of the synthetic thymopoietin II (32-49). The [Gln38, Thr43, Val47]-thymopoietin II (32-49) was approximately equipotent with the synthetic thymopoietin II (32-49) at a concentration of 100 μg/ml.

  十八肽H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH，对应于牛胸腺生成素II修订后的氨基酸序列的第32至49位，通过三个片段(32-36)、(37-41)和(42-49)的叠氮化物缩合合成，随后在茴香硫醚-邻甲酚存在下用氢氟酸脱保护。体外添加合成的胸腺生成素II(32-49)显著恢复了来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力至正常水平。[Gln38, Thr43, Val47]胸腺生成素II(32-49)对来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力的影响也与合成的胸腺生成素II(32-49)进行了比较。在100 μg/ml的浓度下，[Gln38, Thr43, Val47]胸腺生成素II(32-49)与合成的胸腺生成素II(32-49)大致等效。
• Synthesis of calf thymosin .BETA.4 fragment 16-38 and its effect on the impaired blastogenic response of T-lymphocytes of a uremic patient with pneumonia.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.35.3757

  日期：——

  Thymosin β4 fragment 16-38, H-Lys-Leu-Lys-Lys-Thr-Glu-Thr-Gln-Glu-Lys-Asn-Pro-Leu-Pro-Ser-Lys-Glu-Thr-Ile-Glu-Gln-Glu-Lys-OH, was synthesized by a solution method, by assembling five peptide fragments followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The synthetic tricosapeptide was tested for effect on the impaired blastogenic response of phytohemagglutinin-stimulated T-lymphocytes of a uremic patient with pneumonia. The synthetic tricosapeptide was found to have restoring activity, which was approximately equal in potency to that of our synthetic deacetyl-thymosin β4.

  胸腺素β4片段16-38，H-赖氨酸-亮氨酸-赖氨酸-赖氨酸-苏氨酸-谷氨酸-苏氨酸-谷氨酰胺-谷氨酸-赖氨酸-天冬酰胺-脯氨酸-亮氨酸-脯氨酸-丝氨酸-赖氨酸-谷氨酸-苏氨酸-异亮氨酸-谷氨酸-谷氨酰胺-谷氨酸-赖氨酸-OH，通过溶液法合成，采用五个肽片段组装，随后以三氟乙酸中的1 M三氟甲磺酸-硫代茴香醚进行脱保护。合成的二十三肽被测试其对肺炎尿毒症患者经植物血凝素刺激的T淋巴细胞受损的增殖反应的影响。发现合成的二十三肽具有恢复活性，其效力与我们合成的去乙酰基胸腺素β4大致相当。
• 6-Nitro-1-β-napthalenesulfonyloxybenzotriazole : A novel coupling reagent for peptide synthesis
  作者：Balekudru Devadas、Bijoy Kundu、Alka Srivastava、Krishna B Mathur

  DOI：10.1016/0040-4039(93)85069-9

  日期：1993.10

  Synthesis of 6-nitro-1-β-napthalenesulfonyloxybenzotriazole (N-NSBt) and its application as a peptide coupling reagent is being reported. It has been found to be suitable for rapid and quantitative synthesis of optically pure peptides in a stepwise manner.

  报道了6-硝基-1-β-萘磺酰氧基苯并三唑（N-NSBt）的合成及其作为肽偶联剂的应用。已经发现它适合以逐步的方式快速和定量地合成光学纯的肽。
• Synthesis of six common amino acid sequence fragments of thymosins .BETA.4, .BETA.8 and .BETA.9 and determination of their effects on the low E-rosette forming cells of lupus nephritis patients.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.32.228

  日期：——

  Six common amino acid sequence fragments of thymosins β4, β8 and β9, H-Lys-Leu-Lys-Lys-Thr-Glu-Thr-Gln-Glu-Lys-Asn-OH (positions 16-26), H-Lys-Glu-Thr-Ile-Glu-Gln-Glu-Lys-Gln-OH (positions 31-39), H-Asp-Lys-Pro-Asp-OH (positions 2-5), H-Phe-Asp-Lys-OH (positions 12-14), H-Leu-Pro-OH (positions 28-29) and H-Glu-Ile-OH (positions 8-9), were synthesized by the solution method, and were tested to determine their effects on the low E-rosette forming cells of lupus nephritis patients. Two of the fragments, H-Lys-Leu-Lys-Lys-Thr-Glu-Thr-Gln-Glu-Lys-Asn-OH and H-Lys-Glu-Thr-Ile-Glu-Gln-Glu-Lys-Gln-OH, increased E-rosette forming capacity when incubated in vitro with patient's blood though they were less effective than thymosin β9, but the other four peptide fragments, H-Asp-Lys-Pro-Asp-OH, H-Phe-Asp-Lys-OH, H-Leu-Pro-OH and H-Glu-Ile-OH, had no effect.

  胸腺素β4、β8和β9常见的六种氨基酸序列片段，即H-Lys-Leu-Lys-Lys-Thr-Glu-Thr-Gln-Glu-Lys-Asn-OH(第16-26位)，H-Lys-Glu-Thr-Ile-Glu-Gln-Glu-Lys-Gln-OH(第31-39位)，H-Asp-Lys-Pro-Asp-OH(第2-5位)，H-Phe-Asp-Lys-OH(第12-14位)，H-Leu-Pro-OH(第28-29位)和H-Glu-Ile-OH(第8-9位)，采用液相法合成，并检测它们对狼疮肾炎患者低E花环形成细胞的影响。其中两个片段，H-Lys-Leu-Lys-Lys-Thr-Glu-Thr-Gln-Glu-Lys-Asn-OH和H-Lys-Glu-Thr-Ile-Glu-Gln-Glu-Lys-Gln-OH，与患者血液在体外孵育后增加了E花环形成能力，尽管效果不如胸腺素β9，但另外四个肽片段，H-Asp-Lys-Pro-Asp-OH，H-Phe-Asp-Lys-OH，H-Leu-Pro-OH和H-Glu-Ile-OH，则没有效果。