Boc-Gly-Gly-Gly-OBzl | 67585-90-4

• 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: Boc-Gly-Gly-Gly-OBzl
• 英文别名: Benzyl 2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]acetate
• CAS: 67585-90-4
• 化学式: C₁₈H₂₅N₃O₆
• 分子量: 379.413
• InChiKey: QNJAKSVUBBLHTF-UHFFFAOYSA-N

物化性质

• 沸点：
  629.9±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Gly-Gly-Gly-OBzl 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 N-[N-[N-[叔丁氧羰基]甘氨酰]甘氨酰]甘氨酸
  参考文献：
  名称：

  Conformations in the Solid State and Solubility Properties of Protected Homooligopeptides of Glycine and β-Alanine

  摘要：

  在固态下对Boc–Glyn–OBzl（n=3–7）和Boc–(β-Ala)n–OBzl（n=3–8）进行了红外光谱构象分析，结果表明较高聚体（n=5–8）中存在β-折叠结构。溶解度数据显示，Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl在高度极性溶剂中的不溶性分别从六肽和七肽水平开始。保护性同聚肽Gly和β-Ala的不溶性估计是由β-折叠聚集引起的。Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl（n≥5）形成β-折叠结构的高潜力可以明显归因于β-折叠结构中每个Gly和β-Ala残基肽骨架二面角的大自由度。还讨论了蛋白质表面区域中少量Gly残基被β-Ala残基替代的意义。

  DOI：

  10.1246/bcsj.59.3553
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)glycylglycine benzyl ester 在 N-甲基吗啉 、 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Boc-Gly-Gly-Gly-OBzl
  参考文献：
  名称：

  Conformations in the Solid State and Solubility Properties of Protected Homooligopeptides of Glycine and β-Alanine

  摘要：

  在固态下对Boc–Glyn–OBzl（n=3–7）和Boc–(β-Ala)n–OBzl（n=3–8）进行了红外光谱构象分析，结果表明较高聚体（n=5–8）中存在β-折叠结构。溶解度数据显示，Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl在高度极性溶剂中的不溶性分别从六肽和七肽水平开始。保护性同聚肽Gly和β-Ala的不溶性估计是由β-折叠聚集引起的。Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl（n≥5）形成β-折叠结构的高潜力可以明显归因于β-折叠结构中每个Gly和β-Ala残基肽骨架二面角的大自由度。还讨论了蛋白质表面区域中少量Gly残基被β-Ala残基替代的意义。

  DOI：

  10.1246/bcsj.59.3553

文献信息

• Optimum Cross-linking Spacer Length of Dimeric Neurokinin B Analogs for Interaction with NK-1 Tachykinin Receptors.
  作者：Hiroshi Matsumoto、Yasuyuki Shimohigashi、Yukio Takano、Kazuyasu Sakaguchi、Hiro-o Kamiya、Motonori Ohno

  DOI：10.1246/bcsj.66.196

  日期：——

  A series of dimeric analogs of neurokinin B (NKB) COOH-terminal heptapeptide were synthesized in order to find an optimum length of cross-linking spacer for bivalent interaction with tachykinin receptors. Dimerization was carried out at the NH2-terminus of heptapeptide with succinyl bis[(Gly)n–OH], in which the number of glycine varies from 0 to 4. Dimers D–(Gly)n–NKB4—10, namely succinyl bis[(Gly)n–Asp–Ser–Phe–Val–Gly–Leu–Met–NH2] (n = 0—4), were almost inactive in the assay using rat vas deferens, indicating that they have no interaction with NK-2 receptor subtype. In contrast, these dimers were very active in guinea pig ileum (GPI) containing all of NK-1, 2, and 3 receptors. Relative activity was highest when the cross-linking spacer with oligoglycine of n = 2, and decreased sharply for dimers with shorter and longer chain lengths (n = 0 and 1; 3 and 4). In order to specify receptor subtype (NK-1 or NK-3) in GPI to which dimers bind, dimers were examined under the conditions that NK-1 receptors are desensitized by substance P methyl ester. All dimers exhibited drastically diminished contractile activity, indicating that dimers exclusively interact with NK-1. This was further confirmed by blocking the response of NK-3 receptors with atropine, which had no effect on the contractile activity of dimers. The results suggested that dimers interact bivalently with NK-1 receptors by bridging adjacent two binding sites.

  为寻找与速激肽受体二价相互作用的最佳连接间隔长度，合成了一系列神经激肽B（NKB）羧基端七肽的二聚体类似物。通过琥珀酰双[甘氨酸（n）—OH]在七肽的氨基端进行二聚化，其中甘氨酸的数目从0到4变化。二聚体D–（甘氨酸）n–NKB4—10，即琥珀酰双[甘氨酸（n）–天冬氨酸–丝氨酸–苯丙氨酸–缬氨酸–甘氨酸–亮氨酸–蛋氨酸–NH2]（n = 0—4），在利用大鼠输精管进行的实验中几乎无活性，表明它们与NK-2受体亚型无相互作用。相比之下，这些二聚体在含有所有NK-1、NK-2和NK-3受体的大鼠回肠（GPI）中非常活跃。当连接间隔为n = 2的寡甘氨酸时，相对活性最高，而链长更短和更长的二聚体（n = 0和1；3和4）活性显著降低。为了明确二聚体在GPI中结合的受体亚型（NK-1或NK-3），在NK-1受体被甲酯化的P物质脱敏的条件下检测了二聚体。所有二聚体的收缩活性都急剧降低，表明二聚体专门与NK-1受体相互作用。进一步通过利用阿托品阻断NK-3受体的反应，证实了这一点，阿托品对二聚体的收缩活性没有影响。结果表明，二聚体通过桥接相邻的两个结合位点与NK-1受体发生二价相互作用。
• Conformations in the Solid State and Solubility Properties of Protected Homooligopeptides of Glycine and β-Alanine
  作者：Mitsuaki Narita、Masamitsu Doi、Koji Kudo、Yusuke Terauchi

  DOI：10.1246/bcsj.59.3553

  日期：1986.11

  IR spectroscopic conformational analyses of Boc–Glyn–OBzl (n=3–7) and Boc–(β-Ala)n–OBzl (n=3–8) were performed in the solid state, suggesting the occurrence of the β-sheet structure in the higher oligomers (n=5–8). Solubility data indicate that insolubilities of Boc–Glyn–OBzl and Boc–(β-Ala)n–OBzl in high-polar solvents begin at hexa- and heptapeptide levels, respectively. Insolubility of protected homooligopeptides of Gly and β-Ala was estimated to be caused by β-sheet aggregation. The high potential for the β-sheet formation of Boc–Glyn–OBzl and Boc–(β-Ala)n–OBzl (n≥5) could clearly be attributed to the great freedom of the peptide backbone dihedral angles of each of the Gly and β-Ala residues in the β-sheet structure. The implications of a replacement of a few Gly residues with β-Ala residues in surface regions of proteins are also discussed.

  在固态下对Boc–Glyn–OBzl（n=3–7）和Boc–(β-Ala)n–OBzl（n=3–8）进行了红外光谱构象分析，结果表明较高聚体（n=5–8）中存在β-折叠结构。溶解度数据显示，Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl在高度极性溶剂中的不溶性分别从六肽和七肽水平开始。保护性同聚肽Gly和β-Ala的不溶性估计是由β-折叠聚集引起的。Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl（n≥5）形成β-折叠结构的高潜力可以明显归因于β-折叠结构中每个Gly和β-Ala残基肽骨架二面角的大自由度。还讨论了蛋白质表面区域中少量Gly残基被β-Ala残基替代的意义。
• Development of Supramolecular Organo-Gel Based on Tripeptide Skeletons
  作者：Eriko Azuma、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1248/cpb.58.680

  日期：——

  Boc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of antiparallel β-sheets through intermolecular hydrogen bonding was central to the generation of nanofibers during gelation.

  Boc-Ser-Val-Gly-OCH2Ph (31) 在芳香族溶剂中显示出强大的成胶能力，尤其是在甲苯中。31在甲苯中的最低成胶浓度为10 mg/ml，这意味着每分子三肽31固定了2500个甲苯分子。傅里叶变换红外光谱数据显示，通过分子间氢键形成反平行β-折叠是成胶过程中产生纳米纤维的关键。
• Oligoglycine compound, fibrous microtube of oligoglycine compound and
  申请人：Director-General of Agency of Industrial Science and Technology

  公开号：US06030640A1

  公开（公告）日：2000-02-29

  A lipid represented by the following formula: MO--(CO--CH.sub.2 --NH).sub.p --CO--(CH.sub.2).sub.n --CO--(NH--CH.sub.2 --CO).sub.q --OM wherein M represents a hydrogen atom or an alkali metal, n is an integer of 6-18 and p and q each represent an integer of at least 1 with the proviso that a total of p and q is not greater than 6. When an aqueous solution of an alkali metal salt of the lipid is allowed to stand for 2-3 weeks, a fibrous microtube including a tubular body having a diameter of 1-3 .mu.m and a plurality of spherical vesicles contained within the tubular body and having a diameter of 0.1-3 .mu.m is formed.

  以下是化学式表示的脂质：MO--(CO--CH.sub.2 --NH).sub.p --CO--(CH.sub.2).sub.n --CO--(NH--CH.sub.2 --CO).sub.q --OM，其中M代表氢原子或碱金属，n为6-18的整数，p和q各代表至少1的整数，但p和q的总和不大于6。当碱金属盐的水溶液静置2-3周时，形成了一根纤维状微管，包括一个直径为1-3μm的管状体和多个直径为0.1-3μm的球形囊泡包含在管状体内。
• Fibrous microtube of oligoglycine compound
  申请人：Director-General of Agency of Industrial Science And Technology

  公开号：US05876748A1

  公开（公告）日：1999-03-02

  A lipid represented by the following formula: MO--(CO--CH.sub.2 --NH).sub.p --CO--(CH.sub.2).sub.n --CO--(NH--CH.sub.2 --CO).sub.q --OM wherein M represents a hydrogen atom or an alkali metal, n is an integer of 6-18 and p and q each represent an integer of at least 1 with the proviso that a total of p and q is not greater than 6. When an aqueous solution of an alkali metal salt of the lipid is allowed to stand for 2-3 weeks, a fibrous microtube including a tubular body having a diameter of 1-3 .mu.m and a plurality of spherical vesicles contained within the tubular body and having a diameter of 0.1-3 .mu.m is formed.

  以下是所表示的脂质的化学式：MO--(CO--CH.sub.2 --NH).sub.p --CO--(CH.sub.2).sub.n --CO--(NH--CH.sub.2 --CO).sub.q --OM，其中M代表氢原子或碱金属，n是6-18的整数，p和q分别表示至少为1的整数，但p和q的总和不大于6。当允许碱金属盐的水溶液静置2-3周时，会形成一个纤维状微管，包括一个直径为1-3微米的管状体和多个直径为0.1-3微米的球形囊泡包含在管状体内。