H-Pro-NHNH-Boc | 64851-33-8

• 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: H-Pro-NHNH-Boc
• 英文别名: H-Pro-NHNHBoc；tert-butyl N-[[(2S)-pyrrolidine-2-carbonyl]amino]carbamate
• CAS: 64851-33-8
• 化学式: C₁₀H₁₉N₃O₃
• 分子量: 229.279
• InChiKey: SFKNIJNAGXWCBU-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Pro-NHNH-Boc 在 钯 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 Z-Arg(NO2)-Leu-Pro-NHNHBoc
  参考文献：
  名称：

  Human chorionic gonadotropin. II. Synthesis of a hexadecapeptide corresponding to the C-terminal sequence 132-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).

  摘要：

  通过片段缩合法逐步合成了 H-Arg-Leu-Pro-Gly-Pro-Asn-Thr-Pro-Ile-Leu-Pro-Gln-Ser-Leu-Pro-OH 六十肽，对应于 Carlsen 等人提出的 hCG-β C 端序列 132-147、通过片段缩合逐步合成了五个片段[Z-Arg(NO2)-Leu-Pro-NHNHBoc、Z-Gly-Pro-Pro-NHNHBoc、Z-Asn-Thr-Pro-NHNHBoc、Z-Ile-Leu-Pro-NHNHBoc 和 Z-Gln-Ser-Leu-Pro-OBut]。

  DOI：

  10.1248/cpb.28.2692
• 作为产物：
  描述：

  Z-Pro-NHNHBoc 在 20percent Pd(OH)2/C 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到H-Pro-NHNH-Boc
  参考文献：
  名称：

  Synthesis of an l-proline modified mimetic of the A83586C antitumour cyclodepsipeptideElectronic supplementary information (ESI) available: characterisation data. See http://www.rsc.org/suppdata/cc/b2/b204018b/

  摘要：

  通过涉及二肽 9、8 和 7 的三段偶联方案合成了 A83586C 环二肽的模拟物；与我们之前合成 A83586C 时 HATU 介导的大内酰胺化反应 25% 的收率不同，仲氨基酸 18 的相应大内酰胺化反应的收率约为 78%。

  DOI：

  10.1039/b204018b

文献信息

• Amino Acids and Peptides. XVI. Synthesis of N-Terminal Tetrapeptide Analogy of Fibrin .ALPHA.-Chain and Their Inhibitory Effects on Fibrinogen/Thrombin Clotting.
  作者：Koichi KAWASAKI、Katsuhiko HIRASE、Masanori MIYANO、Toshiki TSUJI、Masanori IWAMOTO

  DOI：10.1248/cpb.40.3253

  日期：——

  N-Terminal tetrapeptide analogs of fibrin α-chain were synthesized by the solution method using a new active ester, the ester of the oxime of p-nitroacetophenone, and by the solid-phase method. Their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic peptides, amide analogs of Gly-Pro-Arg-Pro exhibited a more potent inhibitory effect.

  采用溶液法和固相法合成了纤维蛋白α链的N端四肽类似物，使用了一种新的活性酯，即对硝基乙酰苯酮的腙酯。考察了它们对纤维蛋白原/凝血酶凝固的抑制作用。在合成的肽中，甘氨酸-脯氨酸-精氨酸-脯氨酸的酰胺类似物表现出更强的抑制效果。
• Amino Acids and Peptides. XXXV. Synthesis of Mouse Metallothionein I.(2). Synthesis of a Nonacosapeptide Corresponding to N-Terminal Sequence 1-29(.BETA.-Fragment) of Mouse Metallothionein I and Related Petides and Examination of Their Heavy Metal-Binding Properties.
  作者：Satoshi MATSUMOTO、Yasuhiro NISHIYAMA、Yoshio OKADA、Kyong-Son MIN、Satomi ONOSAKA、Keiichi TANAKA

  DOI：10.1248/cpb.40.2701

  日期：——

  A nonacosapeptide corresponding to the N-terminal sequence 1-29 (beta-fragment) of mouse metallothionein I and related peptides were synthesized by the conventional solution method and their heavy metals (Cu2+, Cu+ and Cd2+)-binding properties were examined. The Cu(2+)- or Cu(+)-binding activities of various peptides were not greatly dependent on the peptide structure, so far as examined, as in the

  通过常规溶液法合成了与小鼠金属硫蛋白I的N端序列1-29（β片段）相对应的非糖肽和相关肽，并研究了它们与重金属（Cu2 +，Cu +和Cd2 +）的结合特性。到目前为止，与N. crassa MT和A. bisporus MT的情况一样，各种肽的Cu（2 +）-或Cu（+）结合活性并不很大地依赖于肽结构。相反，这些肽的Cd（2+）结合活性是相当结构依赖性的。
• 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。
• Yoshio, Okada; Iguchi, Shin; Mimura, Masashi, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 9, p. 2707 - 2713
  作者：Yoshio, Okada、Iguchi, Shin、Mimura, Masashi、Kawasaki, Koichi、Yamaji, Kenji、et. al.

  DOI：——

  日期：——