rac-2-amino-3-(trimethylgermyl)propionic acid ethyl ester | 359766-50-0

• 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: rac-2-amino-3-(trimethylgermyl)propionic acid ethyl ester
• 英文别名: Ethyl 2-amino-3-trimethylgermylpropanoate
• CAS: 359766-50-0
• 化学式: C₈H₁₉GeNO₂
• 分子量: 233.834
• InChiKey: LOAJPFTZWYFRLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-2-amino-3-(trimethylgermyl)propionic acid ethyl ester 在 盐酸 、 methyloxirane 作用下， 以 盐酸 为溶剂， 以85%的产率得到rac-2-amino-3-(trimethylgermyl)propionic acid
  参考文献：
  名称：

  Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of d-H2NCH(CH2SiMe3)COOH and d-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: a study on C/Si/Ge bioisosterism

  摘要：

  Two novel efficient methods for the synthesis of racemic silicon- and germanium-containing a-amino acids of the formula type rac-H2NCH(CH2EIR3)COOH (El = Si, Ge; R = organyl), starting from 3,6-diethoxy-2,5-dihydropyrazine, have been developed. Racemic cc-amino acids synthesized: rac-H2NCH(CH2SiMe3)COOH (rac-2), rac-H2NCH(CH2GeMe3)COOH (rac-3), rac-H2NCH(CH2SiMe2Ph)COOH (rac-4), rac-H2NCH(CH2GeMe2Ph)COOH (rac-5), and rac-H2NCH(CH2SiMe2CH=CH2)COOH (rac-6). Preparative liquid-chromatographic resolution of rac-2 and rac-3 [CHIROBIOTIC T (glycopeptide Teicoplanin covalently linked to spherical silica gel) as the stationary phase] yielded the alpha -amino acids (R)-2, (S)-2, (R)-3, and (S)-3. The (R)- and (S)-enantiomers of beta-(trimethylsilyl)alanine [(R)- and (S)-2] and beta-(trimethylgermyl)alanine I(R)- and (S)-3] are sila-analogs and germa-analogs, respectively, of the antipodes of the non-proteinogenic alpha -amino acid beta -tert-butylalanine [(S)- and (R)-H2NCH(CH2CMe3)COOH; (S)- and (R)-1]. Starting from the N-Fmoc-protected C/Si/Ge-analogous (D-configurated) alpha -amino acids (R)-1, (S)-2, and (S)-3, the C/Si/Ge-analogous decapeptides 7-9 [Ac-D-Nal(1)-4-Cl-D-Phe(2)-D-Pal(3)-Ser(4)-N-Me-Tyr(5)-D-Hci(6)- Nle(7)-Arg(8)-Pro(9)-D-Me(3)El-Ala(10)-NH2 (7, El = C; 8, El = Si; 9, El = Ge)] were prepared by sequential solid-phase synthesis. The decapeptides 7-9 were studied in vitro in a functional assay using a recombinant cell line expressing the human GnRH receptor (agonist Triptorelin). Compounds 7-9 behaved as medium-potent GnRH antagonists, the antagonistic potencies of these three C/Si/Ge analogs being very similar. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00783-5
• 作为产物：
  描述：

  氯甲基三甲基锗烷 、 3,6-Diethoxy-2,5-dihydropyridazin 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到rac-2-amino-3-(trimethylgermyl)propionic acid ethyl ester
  参考文献：
  名称：

  Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of d-H2NCH(CH2SiMe3)COOH and d-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: a study on C/Si/Ge bioisosterism

  摘要：

  Two novel efficient methods for the synthesis of racemic silicon- and germanium-containing a-amino acids of the formula type rac-H2NCH(CH2EIR3)COOH (El = Si, Ge; R = organyl), starting from 3,6-diethoxy-2,5-dihydropyrazine, have been developed. Racemic cc-amino acids synthesized: rac-H2NCH(CH2SiMe3)COOH (rac-2), rac-H2NCH(CH2GeMe3)COOH (rac-3), rac-H2NCH(CH2SiMe2Ph)COOH (rac-4), rac-H2NCH(CH2GeMe2Ph)COOH (rac-5), and rac-H2NCH(CH2SiMe2CH=CH2)COOH (rac-6). Preparative liquid-chromatographic resolution of rac-2 and rac-3 [CHIROBIOTIC T (glycopeptide Teicoplanin covalently linked to spherical silica gel) as the stationary phase] yielded the alpha -amino acids (R)-2, (S)-2, (R)-3, and (S)-3. The (R)- and (S)-enantiomers of beta-(trimethylsilyl)alanine [(R)- and (S)-2] and beta-(trimethylgermyl)alanine I(R)- and (S)-3] are sila-analogs and germa-analogs, respectively, of the antipodes of the non-proteinogenic alpha -amino acid beta -tert-butylalanine [(S)- and (R)-H2NCH(CH2CMe3)COOH; (S)- and (R)-1]. Starting from the N-Fmoc-protected C/Si/Ge-analogous (D-configurated) alpha -amino acids (R)-1, (S)-2, and (S)-3, the C/Si/Ge-analogous decapeptides 7-9 [Ac-D-Nal(1)-4-Cl-D-Phe(2)-D-Pal(3)-Ser(4)-N-Me-Tyr(5)-D-Hci(6)- Nle(7)-Arg(8)-Pro(9)-D-Me(3)El-Ala(10)-NH2 (7, El = C; 8, El = Si; 9, El = Ge)] were prepared by sequential solid-phase synthesis. The decapeptides 7-9 were studied in vitro in a functional assay using a recombinant cell line expressing the human GnRH receptor (agonist Triptorelin). Compounds 7-9 behaved as medium-potent GnRH antagonists, the antagonistic potencies of these three C/Si/Ge analogs being very similar. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00783-5

文献信息

• Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of d-H2NCH(CH2SiMe3)COOH and d-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: a study on C/Si/Ge bioisosterism
  作者：Markus Merget、Kurt Günther、Michael Bernd、Eckhard Günther、Reinhold Tacke

  DOI：10.1016/s0022-328x(01)00783-5

  日期：2001.5

  Two novel efficient methods for the synthesis of racemic silicon- and germanium-containing a-amino acids of the formula type rac-H2NCH(CH2EIR3)COOH (El = Si, Ge; R = organyl), starting from 3,6-diethoxy-2,5-dihydropyrazine, have been developed. Racemic cc-amino acids synthesized: rac-H2NCH(CH2SiMe3)COOH (rac-2), rac-H2NCH(CH2GeMe3)COOH (rac-3), rac-H2NCH(CH2SiMe2Ph)COOH (rac-4), rac-H2NCH(CH2GeMe2Ph)COOH (rac-5), and rac-H2NCH(CH2SiMe2CH=CH2)COOH (rac-6). Preparative liquid-chromatographic resolution of rac-2 and rac-3 [CHIROBIOTIC T (glycopeptide Teicoplanin covalently linked to spherical silica gel) as the stationary phase] yielded the alpha -amino acids (R)-2, (S)-2, (R)-3, and (S)-3. The (R)- and (S)-enantiomers of beta-(trimethylsilyl)alanine [(R)- and (S)-2] and beta-(trimethylgermyl)alanine I(R)- and (S)-3] are sila-analogs and germa-analogs, respectively, of the antipodes of the non-proteinogenic alpha -amino acid beta -tert-butylalanine [(S)- and (R)-H2NCH(CH2CMe3)COOH; (S)- and (R)-1]. Starting from the N-Fmoc-protected C/Si/Ge-analogous (D-configurated) alpha -amino acids (R)-1, (S)-2, and (S)-3, the C/Si/Ge-analogous decapeptides 7-9 [Ac-D-Nal(1)-4-Cl-D-Phe(2)-D-Pal(3)-Ser(4)-N-Me-Tyr(5)-D-Hci(6)- Nle(7)-Arg(8)-Pro(9)-D-Me(3)El-Ala(10)-NH2 (7, El = C; 8, El = Si; 9, El = Ge)] were prepared by sequential solid-phase synthesis. The decapeptides 7-9 were studied in vitro in a functional assay using a recombinant cell line expressing the human GnRH receptor (agonist Triptorelin). Compounds 7-9 behaved as medium-potent GnRH antagonists, the antagonistic potencies of these three C/Si/Ge analogs being very similar. (C) 2001 Elsevier Science B.V. All rights reserved.