Z-l-天门冬氨酸-4-苄基 1-(4-硝基苯基)酯 | 2419-54-7

• 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
• 中文名称: Z-l-天门冬氨酸-4-苄基 1-(4-硝基苯基)酯
• 中文别名: Z-l-天门冬氨酸-4-苄基1-(4-硝基苯基)酯；Z-L-天冬氨酸4-苄基1-(4-硝基苯基)酯；Z-L-天冬氨酸Β-苄基Α-(4-硝基苯基)酯
• 英文名称: Z-Asp(OBzl)-ONp
• 英文别名: N-(benzyloxycarbonyl)-β-benzyl-L-aspartic acid p-nitrophenyl ester；Z-L-aspartic acid 4-benzyl 1-(4-nitrophenyl) ester；4-O-benzyl 1-O-(4-nitrophenyl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate
• CAS: 2419-54-7
• 化学式: C₂₅H₂₂N₂O₈
• mdl: MFCD00057618
• 分子量: 478.458
• InChiKey: PDNCLFWZMMRDCA-QFIPXVFZSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  673.8±55.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  Z-l-天门冬氨酸-4-苄基 1-(4-硝基苯基)酯 在 吡啶 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-Benzyloxycarbonyl-β-benzyl-L-aspartyl-D-alaninol-acetat
  参考文献：
  名称：

  Aspartyl amide sweetening agents

  摘要：

  公开了一种化学式为：##EQU1##的酯化合物，其中R.sup.1是氢或羟基，R.sup.2是碳原子数为1至5的烷基、碳原子数为2至3的烯烃基、碳原子数为3至5的环烷基或碳原子数为4至6的甲基环烷基，Y是碳原子数为1至4的亚烷基。还公开了制备该化合物[I]的几种方法。该化合物[I]可用作非营养甜味剂。

  公开号：

  US03971822A1
• 作为产物：
  描述：

  对硝基苯酚 、 CBZ-L-天门冬氨酸β-苄酯 在 N,N'-二环己基碳二亚胺 作用下， 生成 Z-l-天门冬氨酸-4-苄基 1-(4-硝基苯基)酯
  参考文献：
  名称：

  肽合成的新方法。二。邻硝基苯基亚磺酰基用于保护氨基的进一步实例。

  摘要：

  DOI：

  10.1021/ja01079a018

文献信息

• Structure-taste Relationship of Novel α-L-Aspartyl Dipeptide Sweetners
  作者：Muneji Miyoshi、Ken-ichi Nunami、Hiroshi Sugano、Toshiyuki Fujii

  DOI：10.1246/bcsj.51.1433

  日期：1978.5

  A sweetness potency was found in novel α-L-aspartyl dipeptide analogs which were quite stable on heating in an aqueous solution. The insertion of a methylene group into the peptide chain of α-L-aspartyl dipeptide esters mostly decreased the potency of the sweetness. However, the further exchange of the carbonyl and oxygen functions with each other on the ester group of a C-terminal β-alkyl-β-aminopropionic

  在新型 α-L-天冬氨酰二肽类似物中发现了甜味效力，其在水溶液中加热时非常稳定。将亚甲基插入到 α-L-天冬氨酰二肽酯的肽链中主要降低了甜味的效力。然而，发现在 C-末端 β-烷基-β-氨基丙酸的酯基上进一步交换羰基和氧官能团会增加甜度。因此，N-(α-L-天冬氨酰)-O-新戊酰-D-丙氨醇、N-(α-L-天冬氨酰)-O-环丁基羰基-D-丙氨醇和N-(α-L-天冬氨酰)-O-环丙基羰基-D-丙氨醇均是蔗糖的200倍以上。
• Enzymatic synthesis of cholecystokinin-octapeptide.
  作者：KIYOSHI SAKINA、KEIKO KAWAZURA、KAZUYUKI MORIHARA、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.3915

  日期：——

  Cholecystokinin-octapeptide was synthesized by enzymatic condensations of three fragments, without side-chain protection, except for Tyr. Fmoc-Asp-Tyr (SO3Ba1/2)-OH, prepared by the concerted action of proteases, followed by pyridinium trifluoroacetylsulfate treatment, was used as the N-terminal fragment. In the final step, the Nα-Fmoc group employed as a sole protecting group was easily removed by base treatment without affecting the SO3 moiety.

  胆囊收缩素八肽通过三段的酶促缩合合成，除了酪氨酸外，没有侧链保护。Fmoc-Asp-Tyr (SO3Ba1/2)-OH 由蛋白酶的协同作用制备而成，随后经过吡啶三氟乙酰硫酸处理，用作N端片段。在最后一步中，作为唯一保护基团的Nα-Fmoc基团通过碱处理轻松去除，而不影响SO3部分。
• Human chorionic gonadotropin. VI. Synthesis of a tetratriacontapeptide corresponding to the C-terminal sequence 112-145 of the .BETA.-subunit of human chorionic gonadotropin (hCG).
  作者：YOSHIO OKADA、KOICHI KAWASAKI、SHIN IGUCHI、MASAMI YAGYU、KENJI YAMAJI、TETSU TAKAGI、NAGATOSHI SUGITA、OSAMU TANIZAWA

  DOI：10.1248/cpb.29.2851

  日期：——

  The tetratriacontapeptide corresponding to sequence 112-145 of the β-subunit of human chorionic gonadotropin (hCG) was synthesized by assembling peptide fragments by the azide procedure, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). New Zealand white rabbits were immunized with the conjugated antigen in Freund's complete adjuvant. Antiserum capable of 30% specific binding of 125I-hCG or 125I-β-subunit of hCG at a dilution of 1 : 5000 was produced.

  通过叠氮法组装肽片段，然后经反式脂肪酸处理和催化氢化，合成了对应于人绒毛膜促性腺激素（hCG）β亚基序列 112-145 的四三位一体肽。该肽与牛血清白蛋白（BSA）共轭。新西兰白兔在弗罗因德完全佐剂中接合抗原进行免疫。在 1 : 5000 的稀释度下，产生的抗血清能与 125I-hCG 或 hCG 的 125I-β 亚基产生 30% 的特异性结合。
• Amino acids and peptides. XVI. Synthesis of NG-tosylarginyl peptide derivatives-observation of lactam formation of arginyl residue.
  作者：LUIZ JULIANO、MARIA A. JULIANO、ANTONIO DE MIRANDA、SATOSHI TSUBOI、YOSHIO OKADA

  DOI：10.1248/cpb.35.2550

  日期：——

  Z-Arg (Tos) -Pro-NHNHBoc (1) and Z-Arg (Tos) -Val-NHNHBoc (2) were prepared by the DCC, DCC-HOBt, DCC-DNp, mixed anhydride and DPPA methods. In each coupling reaction, lactam formation from the NG-tosylarginyl residue was observed, although the extent of formation was different depending not only on the carboxyl activation method but also on the kind of amino component. Addition of HOBt suppressed the formation of acylurea but did not suppress the formation of the lactam in the synthesis of 2. Addition of DNp suppressed the formation of the lactam slightly although it did not improve the yield of the target peptides. In the mixed anhydride method, a fairly large amount of the lactam was obtained in the synthesis of Z-Arg (Tos) -Pro-NHNHBoc, and a urethan-type derivative, Nα-isobutyloxycarbonyl-Pro-NHNHBoc, was also formed. However, in the case of synthesis of Z-Arg (Tos) -Val-NHNHBoc, lactam formation was suppressed compared with other activation methods and a small amount of urethan-type derivative was obtained. In both cases, the DPPA method gave a fairly good yield of the target peptide with only a trace amount of lactam formation.

  通过 DCC、DCC-HOBt、DCC-DNp、混合酸酐和 DPPA 方法制备了 Z-Arg (Tos) -Pro-NHNHBoc (1)和 Z-Arg (Tos) -Val-NHNHBoc (2)。在每个偶联反应中，都观察到 NG-对甲苯磺酰精氨酰残基形成内酰胺，但形成的程度不仅取决于羧基活化方法，还取决于氨基成分的种类。在合成 2 的过程中，加入 HOBt 能抑制酰基脲的形成，但不能抑制内酰胺的形成；加入 DNp 能轻微抑制内酰胺的形成，但不能提高目标肽的产量。在混合酸酐法中，合成 Z-Arg (Tos) -Pro-NHNHBoc 时得到了相当多的内酰胺，还形成了一种脲烷型衍生物 Nα-isobutyloxycarbonyl-Pro-NHNHBoc 。然而，在合成 Z-Arg (Tos) -Val-NHNHBoc 时，与其他活化方法相比，内酰胺的形成受到抑制，并获得了少量脲烷型衍生物。在这两种情况下，DPPA 方法都能得到相当高产率的目标肽，而且只有微量内酰胺形成。
• Human chorionic gonadotropin. VII. Preparation and immunocharacteristics of carboxyl-terminal peptides of the .BETA.-subunit of human chorionic gonadotropin.
  作者：KOICHI KAWASAKI、SHIN IGUCHI、CHIYE KAWASAKI、MITSUKO MAEDA、YOSHIO OKADA、KENJI YAMAJI、TETSU TAKAGI、NAGATOSHI SUGITA、OSAMU TANIZAWA

  DOI：10.1248/cpb.30.1043

  日期：——

  Various carboxyl-terminal peptides of hCG-β were prepared from the corresponding blocked peptides by TFA treatment followed by hydrogenation. The prepared peptides were tested for inhibitory action on the binding between 125I-hCG and the antiserum against the carboxyl-terminal portion of hCG-β. The results suggest that an antigenic site of this antiserum may exist around the amino-terminal portion of the carboxylterminal hexadecapeptide.

  通过TFA处理和氢化，从相应的封闭肽中制备了hCG-β的各种羧基末端肽。对制备的肽进行了测试，以确定其对125I-hCG与抗hCG-β羧基末端部分的抗血清之间的结合的抑制作用。结果表明，这种抗血清的抗原位点可能存在于羧基末端十六肽的氨基末端部分周围。