Boc-Tyr(Bzl)-D-Ala-Gly-OBzl | 66959-85-1

• 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-Tyr(Bzl)-D-Ala-Gly-OBzl
• 英文别名: Benzyl Nα-t-Butyloxycarbonyl-O-benzyl-L-tyrosyl-D-alanyl-glycinate；Boc-Tyr(Bn)-D-Ala-Gly-OBn；benzyl 2-[[(2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylmethoxyphenyl)propanoyl]amino]propanoyl]amino]acetate
• CAS: 66959-85-1
• 化学式: C₃₃H₃₉N₃O₇
• 分子量: 589.689
• InChiKey: BSOKAULIWLBWHG-LXFBAYGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Tyr(Bzl)-D-Ala-Gly-OBzl 在 钯 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到Boc-酪氨酸-D-丙氨酸-甘氨酸
  参考文献：
  名称：

  Amino Acids and Peptides. XXIV. Preparation and Antinociceptive Effect of (D-Ala2,(N-Me)Phe4)Enkephalin Analog-Poly(Ethylene Glycol) Hybrids.

  摘要：

  通过溶液法制备了氨基聚乙二醇（PEG）和[D-Ala2, (N-Me)Phe4]enkephalin 类似物的混合物，即 H-Tyr-D-Ala-Gly-(Me)Phe-aPEG、H-Tyr-D-Ala-Gly-(Me)Phe-Leu-aPEG 和 H-Tyr-D-Ala-Gly-(Me)Phe-D-Leu-aPEG，并与多肽的抗痛觉特性进行了比较。H-Tyr-D-Ala-Gly-(Me)Phe-OH和H-Tyr-D-Ala-Gly-(Me)Phe-Leu-OH本身在脑内注射（i.c.v.）剂量为10-30nmol/只动物时产生的抗痛觉作用不如静脉注射吗啡（3μg/只动物），而H-Tyr-D-Ala-Gly-(Me)Phe-D-Leu-OH则没有明显的作用。然而，H-Tyr-D-Ala-Gly-(Me)Phe-D-Leu-OH和H-Tyr-D-Ale-Gly-(Me)Phe-D-Leu-OH与aPEG形成杂交后，其抗痛作用明显增强，水平高于3微克/只小鼠吗啡的作用，且作用至少持续120分钟。相比之下，H-Tyr-D-Ala-Gly-(Me)Phe-OH 的作用则因杂交形成而减弱。鉴于 aPEG 的低毒性和弱免疫基因特性，这些杂交化合物可用于缓解慢性和严重疼痛患者的治疗。

  DOI：

  10.1248/cpb.42.1859
• 作为产物：
  描述：

  甘氨酸苄酯盐酸盐 在 盐酸 、 二苯基膦叠氮化物 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 179.0h， 生成 Boc-Tyr(Bzl)-D-Ala-Gly-OBzl
  参考文献：
  名称：

  Novel analogs of enkephalin: identification of functional groups required for biological activity

  摘要：

  Novel tri- and tetrapeptide analogues of enkephalin, in conjunction with earlier structure-activity data, confirm that chemical substitutents present in the first and fourth residues of enkephalin are required for in vitro biological activity. A class of arylamino and alkylamino derivatized tripeptides also were found to have significant in vitro opioid-like activity indistinguishable from [D-Ala2,D-Leu5]enkephalin and morphine.

  DOI：

  10.1021/jm00184a010

文献信息

• Preparation of an affinity gel for opiate receptors.
  作者：Toshiyuki Fujioka、Fumiko Inoue、Masayuki Kuriyama

  DOI：10.1248/cpb.33.4633

  日期：——

  [D-Ala2, Leu5] Enkephalin was coupled with aminohexyl-Sepharose at its C-terminal. This gel could bind solubilized opiate receptors prepared from rat brain using digitonin. This suggests that the prepared gel is a prominent candidate as an affinity gel for opiate receptors.

  [D-Ala2, Leu5] 脑啡肽在其C端的氨基酸己基-琼脂糖上偶联。这种凝胶能够结合使用皂素从大鼠脑中制备的可溶性阿片受体。这表明，制备的凝胶是阿片受体的亲和凝胶的突出候选者。
• Analgesic compounds
  申请人：Eli Lilly and Company

  公开号：US04264491A1

  公开（公告）日：1981-04-28

  Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in which L and D, when applicable, define the chirality; R.sub.1 and R.sub.2 independently are hydrogen or C.sub.1 -C.sub.3 primary alkyl; R.sub.3 is C.sub.1 -C.sub.4 primary or secondary alkyl or --CH.sub.2 CH.sub.2 --S--CH.sub.3 ; R.sub.4 is hydrogen or C.sub.1 -C.sub.3 primary alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 primary alkyl; Y is hydrogen or acetyl; and Z is ##STR2## --CH.sub.2 OH, or --CN; subject to the limitation that no more than one of R.sub.4 and R.sub.5 is C.sub.1 -C.sub.3 primary alkyl; are useful analgesic agents.

  式##STR1##的化合物及其药学上可接受的无毒酸盐，其中L和D在适用时定义手性；R.sub.1和R.sub.2独立地是氢或C.sub.1-C.sub.3初级烷基；R.sub.3是C.sub.1-C.sub.4初级或次级烷基或--CH.sub.2 CH.sub.2 --S--CH.sub.3；R.sub.4是氢或C.sub.1-C.sub.3初级烷基；R.sub.5是氢或C.sub.1-C.sub.3初级烷基；Y是氢或乙酰基；Z是##STR2##--CH.sub.2 OH，或--CN；受限于R.sub.4和R.sub.5中不超过一个是C.sub.1-C.sub.3初级烷基；是有用的镇痛剂。
• SMITHWICK, E. L. ,, JR;FREDERICKSON, R. C. A.;SHUMAN, R. T.
  作者：SMITHWICK, E. L. ,, JR、FREDERICKSON, R. C. A.、SHUMAN, R. T.

  DOI：——

  日期：——
• US4264491A
  申请人：——

  公开号：US4264491A

  公开（公告）日：1981-04-28
• Novel analogs of enkephalin: identification of functional groups required for biological activity
  作者：Fredric A. Gorin、T. M. Balasubramanian、Theodore J. Cicero、John Schwietzer、Garland R. Marshall

  DOI：10.1021/jm00184a010

  日期：1980.10

  Novel tri- and tetrapeptide analogues of enkephalin, in conjunction with earlier structure-activity data, confirm that chemical substitutents present in the first and fourth residues of enkephalin are required for in vitro biological activity. A class of arylamino and alkylamino derivatized tripeptides also were found to have significant in vitro opioid-like activity indistinguishable from [D-Ala2,D-Leu5]enkephalin and morphine.