N-{[(2-甲基-2-丙基)氧基]羰基}苯丙氨酰甘氨酰甘氨酸 | 103340-16-5

• 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: N-{[(2-甲基-2-丙基)氧基]羰基}苯丙氨酰甘氨酰甘氨酸
• 英文名称: Boc-Phe-Gly-Gly
• 英文别名: boc-Phe-Gly-Gly-OH；2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]acetyl]amino]acetic acid
• CAS: 103340-16-5
• 化学式: C₁₈H₂₅N₃O₆
• mdl: MFCD00190819
• 分子量: 379.413
• InChiKey: SEQGOADLZZCJJG-ZDUSSCGKSA-N

物化性质

• 沸点：
  717.9±60.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘代三甲硅烷 、 N-{[(2-甲基-2-丙基)氧基]羰基}苯丙氨酰甘氨酰甘氨酸 在 N,O-双三甲硅基乙酰胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  N-Boc Deprotection and Isolation Method for Water-Soluble Zwitterionic Compounds

  摘要：

  A highly efficient TMSI-mediated deprotection and direct isolation method to obtain zwitterionic compounds from the corresponding N-Boc derivatives has been developed. This method has been demonstrated in the final deprotection/isolation of the beta-lactamase inhibitor MK-7655 as a part of its manufacturing process. Further application of this process toward other zwitterionic compounds, such as dipeptides and tripeptides, has been successfully developed. Furthermore, a catalytic version of this transformation has been demonstrated in the presence of BSA or BSTFA.

  DOI：

  10.1021/jo502319z
• 作为产物：
  描述：

  [2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-acetylamino]-acetic acid benzyl ester 在 钯 乙酸乙酯 作用下， 以 甲醇 为溶剂， 生成 N-{[(2-甲基-2-丙基)氧基]羰基}苯丙氨酰甘氨酰甘氨酸
  参考文献：
  名称：

  Atrial natriuretic peptide derivative

  摘要：

  一种肽衍生物的公式为 ##STR1## 其中A是氢或具有2至18个碳原子的烃基酰基，该烃基酰基在α位上被氨基取代; B是F-Gly，其中F是中性的α-氨基酸残基，或NH-(CH.sub.2)nCO，其中n是1至4的整数; C是中性的α-氨基酸残基; 而E是L-Arg或D-Arg; 当A、B和C为氢、Gly-Gly和Met或Ile时，E为D-Arg，或其药理学上可接受的盐具有强烈的降压和利尿活性; 因此，它可用作治疗高血压、利尿剂、心脏和脑循环疾病的治疗药物。

  公开号：

  US05159061A1

文献信息

• Studies on flavored peptides. VIII. Mechanism for the bitter tasting potency of peptides using O-aminoacyl sugars as model compounds.
  作者：Masahiro TAMURA、Takafumi MIYOSHI、Naoko MORI、Keisuke KINOMURA、Michihiko KAWAGUCHI、Norio ISHIBASHI、Hideo OKAI

  DOI：10.1271/bbb1961.54.1401

  日期：——

  In order to study the role of hydrophobicity in bitter peptides, several O-aminoacyl sugars, in which amino acids or peptides were attached to the 2- and 3-position of methyl α-D-glucopyranoside, were synthesized and sensory analyses were carried out. It was found that the bitterness increased as the hydrophobicity of compounds increased, implying that the bitterness receptor recognizes the hydrophobicity of bitter peptides. A structure for the bitterness receptor is also discussed.

  为了研究疏水性在苦味肽中的作用，合成了几种 O-氨基酰基糖，其中氨基酸或肽附着在甲基 α-D 吡喃葡萄糖苷的 2 位和 3 位上，并进行了感官分析。结果发现，随着化合物疏水性的增加，苦味也随之增加，这意味着苦味受体能识别苦味肽的疏水性。此外，还讨论了苦味受体的结构。
• <i>N</i>-Boc Deprotection and Isolation Method for Water-Soluble Zwitterionic Compounds
  作者：Zhijian Liu、Nobuyoshi Yasuda、Michael Simeone、Robert A. Reamer

  DOI：10.1021/jo502319z

  日期：2014.12.5

  A highly efficient TMSI-mediated deprotection and direct isolation method to obtain zwitterionic compounds from the corresponding N-Boc derivatives has been developed. This method has been demonstrated in the final deprotection/isolation of the beta-lactamase inhibitor MK-7655 as a part of its manufacturing process. Further application of this process toward other zwitterionic compounds, such as dipeptides and tripeptides, has been successfully developed. Furthermore, a catalytic version of this transformation has been demonstrated in the presence of BSA or BSTFA.
• Atrial natriuretic peptide derivative
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05159061A1

  公开（公告）日：1992-10-27

  A peptide derivative of the formula ##STR1## wherein A is hydrogen or a hydrocarbon acyl having 2 to 18 carbon atoms which is substituted by an amino group at the .alpha.-position; B is F-Gly wherein F is a neutral .alpha.-amino acid residue, or NH-(CH.sub.2)nCO wherein n is an integer of 1 to 4; C is a neutral .alpha.-amino acid residue; and E is L-Arg or D-Arg; when A, B and C are hydrogen, Gly-Gly, and Met or Ile, respectively, E is D-Arg, or its pharmacologically acceptable salt has strong hypotensive and natriuretic activity; therefore it is useful as a therapeutic drug for hypertension, a diuretic, and a therapeutic drug for cardiac and cerebral circulatory diseases.

  一种肽衍生物的公式为 ##STR1## 其中A是氢或具有2至18个碳原子的烃基酰基，该烃基酰基在α位上被氨基取代; B是F-Gly，其中F是中性的α-氨基酸残基，或NH-(CH.sub.2)nCO，其中n是1至4的整数; C是中性的α-氨基酸残基; 而E是L-Arg或D-Arg; 当A、B和C为氢、Gly-Gly和Met或Ile时，E为D-Arg，或其药理学上可接受的盐具有强烈的降压和利尿活性; 因此，它可用作治疗高血压、利尿剂、心脏和脑循环疾病的治疗药物。