2-叔丁氧羰基氨基-4-氨基甲酰基丁酸 4-硝基苯酯 | 15387-45-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - BOC-氨基酸
• 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: 2-叔丁氧羰基氨基-4-氨基甲酰基丁酸 4-硝基苯酯
• 中文别名: 叔丁氧羰基-L-谷氨酰胺对硝基苯基酯；2-叔丁氧羰基氨基-4-氨基甲酰基丁酸4-硝基苯酯；Boc-L-谷氨酰胺-4-硝基苯酯；Boc-L-谷氨酸4-硝基苯酯；Boc-L-谷氨酸 4-硝基苯酯
• 英文名称: Boc-Gln-ONp
• 英文别名: Boc-L-Gln-ONP；(4-nitrophenyl) (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 15387-45-8
• 化学式: C₁₆H₂₁N₃O₇
• 分子量: 367.359
• InChiKey: HJMMCTZLXOVMFB-LBPRGKRZSA-N

物化性质

• 熔点：
  146 - 148°C
• 沸点：
  617.5±55.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微超声处理）、甲醇（轻微超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2-叔丁氧羰基氨基-4-氨基甲酰基丁酸 4-硝基苯酯 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (S)-3-氨基-哌啶-2,6-二酮盐酸盐
  参考文献：
  名称：

  Synthesis and antiaggregative activity of derivatives of 3-aminopiperidine-2,6-diones and 3-aminopyrrolidine-2,5-diones

  摘要：

  DOI：

  10.1007/bf02580514
• 作为产物：
  描述：

  N-alpha-叔丁氧羰基-L-谷氨酰胺二环己基铵盐 、 对硝基三氟乙酸苯酯 在 吡啶 作用下， 反应 0.3h， 以78%的产率得到2-叔丁氧羰基氨基-4-氨基甲酰基丁酸 4-硝基苯酯
  参考文献：
  名称：

  Meldal; Kindtler, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 235 - 241

  摘要：

  DOI：

文献信息

• Synthesis of Four Peptide Derivatives to Build the Sequence Corresponding to 31–53 of Human Epidermal Growth Factor (h-EGF)
  作者：Song Yub Shin、Yukihiko Kaburaki、Masanori Watanabe、Eisuke Munekata

  DOI：10.1271/bbb.56.108

  日期：1992.1

  For the classical solution synthesis of human epidermal growth factor (h-EGF), four protected peptide derivatives, Boc-Lys(Cl-Z)-Trp-Trp-Glu(OcHex)-Leu-Arg(Tos)-OBzl (5), Boc-Glu(OcHex)-Arg(Tos)-Cys(MeBzl)-Gln-Tyr(Br-Z)-Arg(Tos)-Asp(OcHex)-Leu-OH (13), Boc-Tyr(Br-Z)-Ile-Gly-OH (16), and Boc-Cys(MeBzl)-Asn-Cys(MeBzl)-Val-Val-Gly-OH (22) were synthesized to build up the sequence corresponding to 31–53.

  对于人表皮生长因子（h-EGF）的经典溶液合成，合成了四种保护肽衍生物：Boc-Lys(Cl-Z)-Trp-Trp-Glu(OcHex)-Leu-Arg(Tos)-OBzl (5)、Boc-Glu(OcHex)-Arg(Tos)-Cys(MeBzl)-Gln-Tyr(Br-Z)-Arg(Tos)-Asp(OcHex)-Leu-OH (13)、Boc-Tyr(Br-Z)-Ile-Gly-OH (16) 和 Boc-Cys(MeBzl)-Asn-Cys(MeBzl)-Val-Val-Gly-OH (22)，以构建对应于31–53的序列。
• Synthesis of a Partial Sequence of Proinsulin Using the A-Chain of Natural Insulin. II. Synthesis of a Peptide Corresponding to Positions 53–81 of Bovine Proinsulin
  作者：Hiroko Aiba、Yasutsugu Shimonishi

  DOI：10.1246/bcsj.53.192

  日期：1980.1

  For the synthesis of bovine proinsulin, the S-sulfonate of the Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A-chain, which was synthesized using the S-sulfonate of the A-chain of natural bovine insulin and which corresponds to positions 53–81 of bovine proinsulin, was coupled with Boc–Ala–Leu–Glu(OBut)–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–N3. After removal of the protecting groups from the resulting material

  对于牛胰岛素原的合成，Leu-Glu-Gly-Pro-Pro-Gln-Lys[Z(2-Cl)]-Arg-A-链的 S-磺酸盐，它是使用 S-磺酸盐合成的天然牛胰岛素的 A 链对应于牛胰岛素原的 53-81 位，与 Boc-Ala-Leu-Glu(OBut)-Leu-Ala-Gly-Gly-Pro-Gly-Ala-Gly-偶联Gly-N3。从所得材料中去除保护基团后，Ala–Leu–Glu–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–Leu–Glu–Gly–Pro–Pro– 的 S-磺酸盐Gln-Lys[Z(2-Cl)]-Arg-A-链，对应于牛胰岛素原的 41-81 位，通过 QAE-Sephadex A-25 色谱纯化。
• C-Terminal deletions in antagonistic analogs of vasopressin that improve their specificities for antidiuretic (V2) and vasopressor (V1) receptors
  作者：Maurice Manning、Aleksandra Misicka、Aleksandra Olma、Wieslaw A. Klis、Krzysztof Bankowski、Eleonora Nawrocka、Marian Kruszynski、Aleksander Kolodziejczyk、Ling Ling Cheng

  DOI：10.1021/jm00395a012

  日期：1987.12

  analogues of arginine-vasopressin (AVP), two highly selective antidiuretic (V2) agonists, four vasopressor (V1) antagonists, and five V2/V1 antagonists. The parent AVP agonists are (1) AVP, (2) 1-deamino[8-D-arginine]vasopressin (dDAVP), and (3) its 4-valine analogue, dVDAVP. The parent V1 antagonists are (4) [1-(beta-mercapto-beta,beta-pentamethylenepropionic acid)] arginine-vasopressin (d(CH2)5AVP)

  我们报告精氨酸升压素（AVP）的12 desGly和12 desGly（NH2）类似物，两个高选择性抗利尿剂（V2）激动剂，四个升压素（V1）拮抗剂和五个V2 / V1拮抗剂的固相合成。亲本AVP激动剂是（1）AVP，（2）1-脱氨基[8-D-精氨酸]加压素（dDAVP）和（3）其4-缬氨酸类似物dVDAVP。亲本V1拮抗剂是（4）[1-（β-巯基-β，β-五亚甲基丙酸）]精氨酸-加压素（d（CH2）5AVP），（5）d（ ）5VDAVP，（6）[1-脱氨基青霉胺，4-缬氨酸，8-D-精氨酸]加压素（dPVDAVP）和（7）d（ ）5 [Tyr（Me）] AVP。亲本V2 / V1拮抗剂是（8）d（ ）5 [D-Phe2，Ile4] AVP，（9）d（ ）5 [D-Phe2] VAVP，（10）d（ ）5 [D- Tyr（Et）2] VAVP，（11）d（ ）5 [Tyr（Et2]
• 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。
• Amino acids and peptides. XXVIII. Synthesis of peptide fragments related to eglin c and studies on the relationship between their structure and effects on human leukocyte elastase, cathepsin G and .ALPHA.-chymotrypsin.
  作者：Satoshi TSUBOI、Kazunori NAKABAYASHI、Yoshikazu MATSUMOTO、Naoki TENO、Yuko TSUDA、Yoshio OKADA、Yoko NAGAMATSU、Junichiro YAMAMOTO

  DOI：10.1248/cpb.38.2369

  日期：——

  Various peptide fragments related to eglin c, which consists of 70 amino acid residues, were synthesized by a conventional solution method and their inhibitory effects on leukocyte elastase, cathepsin G and α-chymotrypsin were examined. Among them, H-Arg-Glu-Tyr-Phe-OMe (eglin c 22-25) and H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe (eglin c 41-49) inhibited cathepsin G and α-chymotrypsin but not leukocyte elastase, while H-Thr-Asn-Val-Val-OMe (eglin c 60-63) inhibited leukocyte elastase but not cathepsin G or α-chymotrypsin, although eglin c potently inhibited leukocyte elastase, cathepsin G and α-chymotrypsin. These results indicated that the interaction sites of eglin c with leukocyte elastase, cathepsin G and α-chymotrypsin might be different.

  采用常规的溶液法合成了与来自家蚕血淋巴的抗蛋白酶eglin c（由70个氨基酸残基构成）相关的各种肽片段，并检验了它们对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的抑制效应。其中，H-Arg-Glu-Tyr-Phe-OMe（eglin c 22-25）和H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe（eglin c 41-49）能抑制组织蛋白酶G和α-胰凝乳蛋白酶，但不能抑制白细胞弹性蛋白酶，而H-Thr-Asn-Val-Val-OMe（eglin c 60-63）能抑制白细胞弹性蛋白酶，但不能抑制组织蛋白酶G或α-胰凝乳蛋白酶，尽管eglin c对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶都具有强抑制作用。这些结果提示，eglin c与白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的相互作用部位可能各不相同。