Ac(L,D)Phe(p-CH3SO3Na) | 128524-87-8

• 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: Ac(L,D)Phe(p-CH3SO3Na)
• 英文别名: sodium N-acetamido-p-(sulfomethyl)-DL-phenylalanine；monosodium N-acetyl-4-sulfonatomethylphenylalanine；Sodium;[4-(2-acetamido-2-carboxyethyl)phenyl]methanesulfonate
• CAS: 128524-87-8
• 化学式: C₁₂H₁₄NO₆S*Na
• 分子量: 323.302
• InChiKey: LLZWXYOAFKWBQF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.13
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ac(L,D)Phe(p-CH3SO3Na) 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 Ac-D-Phe(p-CH2-SO3Na)-Nle-Gly-Trp-Nle-Asp-Phe-NH2
  参考文献：
  名称：

  Full agonists of CCK8 containing a nonhydrolyzable sulfated tyrosine residue

  摘要：

  The sulfate ester of CCK26-33 or CCK8 (Asp-Tyr(SO3H)-Met-Gly-Trp-Met-Asp-Phe-NH2) borne by the tyrosine residue is a critical determinant of the biological activity of this peptide. In order to increase the stability of this molecule, the sulfated tyrosine has been replaced by a synthetic amino acid (L,D)Phe(p-CH2SO3Na) in which the OSO3H group was replaced by the nonhydrolyzable CH2SO3H group. Both isomers were separated by chromatography and the stereochemistry of the Phe(p-CH2SO3Na) residue in each peptide was established by NMR spectroscopy. The biological activities of the new derivatives Ac[X27, Nle28,Nle31]CCK27-33 were compared with those of Boc[Nle28,Nle31]CCK27-33, an equiactive analogue of CCK8 and Boc[D-Tyr(SO3Na)27,Nle28,Nle31]CCK27-33. Besides their highly enhanced chemical stability, Ac[L-Phe(p-CH2SO3Na)27,Nle28,Nle31]CCK27-33 and Ac[D-Phe(p-CH2SO3Na)27,Nle28,Nle31]CCK27-33 display high affinity for peripheral and central CCK receptors (KI congruent to 10(-9) M) and proved to be full agonists in the stimulation of pancreatic secretion as well as in the in vitro CCK8-induced contractions of the guinea pig ileum.

  DOI：

  10.1021/jm00122a026
• 作为产物：
  描述：

  diethyl <4-(chloromethyl)benzyl>acetamidomalonate 在 盐酸 、 溶剂黄146 、 汞 、 sodium sulfite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 Ac(L,D)Phe(p-CH3SO3Na)
  参考文献：
  名称：

  Amino acids and peptides having a modified tyrosine residue, their

  摘要：

  这些化合物由公式(I)表示，其中R.sub.1 R.sub.2 = H，C.sub.1-C.sub.8烷基，C.sub.3-C.sub.7环烷基或芳香基; （当R.sub.1 = H时，R.sub.2可以是胺保护基，氨基酸残基或肽片段; R.sub.1和R.sub.2能够与N形成5-7成分环）; A = 酰基或亚甲基; W = 羟基，苯氧基，C.sub.1-C.sub.8烷氧基; 苯氧基（C.sub.1-C.sub.8烷基），氨基，（C.sub.1-C.sub.8烷基）氨基，二（C.sub.1-C.sub.8烷基）氨基（当A = 酰基，W = 氨基酸残基或肽片段时）; Y = --OSO.sub.2 OR.sub.3 (II)，--OPO(OR.sub.3).sub.2 (III)，--(CH.sub.2(.sub.m--SO.sub.2 OR.sub.3 (IV)或--(CH.sub.2).sub.m--PO(OR.sub.3).sub.2 (V) [R.sub.3 = H，C.sub.1-C.sub.8烷基; m = 1至4]; Z = 环己烷，吡啶基或苯基; n = 0至4; 在Y =（II）或（III）时，-A-W除了由天然氨基酸组成的序列外，还有其他的。它们具有抗精神病作用，促进记忆过程的作用，镇痛作用; 它们有用作厌食剂的作用，并且对肠道蠕动具有刺激作用。##STR1##

  公开号：

  US05190921A1

文献信息

• Amino acids and peptides having a modified tyrosine residue, their
  申请人：Institut National de la Sante et de la Recherche Medicale (INSERM)

  公开号：US05190921A1

  公开（公告）日：1993-03-02

  These compounds are represented by formula (I), in which each of R.sub.1 R.sub.2 =H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, or aromatic; (when R.sub.1 =H, R.sub.2 can be an amine function-protecting radical, amino acid residue or peptide fragment; R.sub.1 and R.sub.2 being capable of forming, with N, a 5-7 component ring); A=carbonyl or methylene; W=hydroxy, phenoxy, C.sub.1 -C.sub.8 alkoxy; phenoxy(C.sub.1 -C.sub.8 alkyl), amino, (C.sub.1 -C.sub.8 alkyl)amino, di(C.sub.1 -C.sub.8 alkyl)amino, (when A=carbonyl, W=amino acid residue or peptide fragment); Y=--OSO.sub.2 OR.sub.3 (II), --OPO(OR.sub.3).sub.2 (III), --(CH.sub.2 (.sub.m --SO.sub.2 OR.sub.3 (IV) or --(CH.sub.2).sub.m --PO(OR.sub.3).sub.2 (V) [R.sub.3 =H, C.sub.1 -C.sub.8 alkyl; m=1 to 4]; Z=cyclohexane, pyridyl or phenyl; n=0 to 4; on the condition that when Y=(II) or (III), -A-W is other than a sequence composed of natural amino acids. They have antipsychotic properties, an effect facilitating the memorization processes, analgesic properties; they are useful as anorexia-producing agents, and they have stimulatory effects on intestinal motility. ##STR1##

  这些化合物由公式(I)表示，其中R.sub.1 R.sub.2 = H，C.sub.1-C.sub.8烷基，C.sub.3-C.sub.7环烷基或芳香基; （当R.sub.1 = H时，R.sub.2可以是胺保护基，氨基酸残基或肽片段; R.sub.1和R.sub.2能够与N形成5-7成分环）; A = 酰基或亚甲基; W = 羟基，苯氧基，C.sub.1-C.sub.8烷氧基; 苯氧基（C.sub.1-C.sub.8烷基），氨基，（C.sub.1-C.sub.8烷基）氨基，二（C.sub.1-C.sub.8烷基）氨基（当A = 酰基，W = 氨基酸残基或肽片段时）; Y = --OSO.sub.2 OR.sub.3 (II)，--OPO(OR.sub.3).sub.2 (III)，--(CH.sub.2(.sub.m--SO.sub.2 OR.sub.3 (IV)或--(CH.sub.2).sub.m--PO(OR.sub.3).sub.2 (V) [R.sub.3 = H，C.sub.1-C.sub.8烷基; m = 1至4]; Z = 环己烷，吡啶基或苯基; n = 0至4; 在Y =（II）或（III）时，-A-W除了由天然氨基酸组成的序列外，还有其他的。它们具有抗精神病作用，促进记忆过程的作用，镇痛作用; 它们有用作厌食剂的作用，并且对肠道蠕动具有刺激作用。##STR1##
• ROQUES, BERNARD PIERRE;MARSEIGNE, ISABELLE;CHARPENTIER, BRUNO
  作者：ROQUES, BERNARD PIERRE、MARSEIGNE, ISABELLE、CHARPENTIER, BRUNO

  DOI：——

  日期：——
• US5190921A
  申请人：——

  公开号：US5190921A

  公开（公告）日：1993-03-02
• Synthesis of new amino acids mimicking sulfated and phosphorylated tyrosine residues
  作者：I. Marseigne、B. P. Roques

  DOI：10.1021/jo00250a043

  日期：1988.7
• Full agonists of CCK8 containing a nonhydrolyzable sulfated tyrosine residue
  作者：I. Marseigne、P. Roy、A. Dor、C. Durieux、D. Pelaprat、M. Reibaud、J. C. Blanchard、B. P. Roques

  DOI：10.1021/jm00122a026

  日期：1989.2

  The sulfate ester of CCK26-33 or CCK8 (Asp-Tyr(SO3H)-Met-Gly-Trp-Met-Asp-Phe-NH2) borne by the tyrosine residue is a critical determinant of the biological activity of this peptide. In order to increase the stability of this molecule, the sulfated tyrosine has been replaced by a synthetic amino acid (L,D)Phe(p-CH2SO3Na) in which the OSO3H group was replaced by the nonhydrolyzable CH2SO3H group. Both isomers were separated by chromatography and the stereochemistry of the Phe(p-CH2SO3Na) residue in each peptide was established by NMR spectroscopy. The biological activities of the new derivatives Ac[X27, Nle28,Nle31]CCK27-33 were compared with those of Boc[Nle28,Nle31]CCK27-33, an equiactive analogue of CCK8 and Boc[D-Tyr(SO3Na)27,Nle28,Nle31]CCK27-33. Besides their highly enhanced chemical stability, Ac[L-Phe(p-CH2SO3Na)27,Nle28,Nle31]CCK27-33 and Ac[D-Phe(p-CH2SO3Na)27,Nle28,Nle31]CCK27-33 display high affinity for peripheral and central CCK receptors (KI congruent to 10(-9) M) and proved to be full agonists in the stimulation of pancreatic secretion as well as in the in vitro CCK8-induced contractions of the guinea pig ileum.