(R)-tert-butoxycarbonylamino-fluorenylmethoxycarbonylaminoacetic acid | 306773-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-tert-butoxycarbonylamino-fluorenylmethoxycarbonylaminoacetic acid
• 英文别名: N-Boc-N'-Fmoc-diaminoacetic acid；Fmoc-a-amino-D-Gly(Boc)-OH；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 306773-83-1
• 化学式: C₂₂H₂₄N₂O₆
• 分子量: 412.442
• InChiKey: AWCFKRJSLGKRNA-GOSISDBHSA-N

物化性质

• 沸点：
  634.6±55.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-tert-butoxycarbonylamino-fluorenylmethoxycarbonylaminoacetic acid 在 三乙烯二胺 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.5h， 生成 (R)-tert-Butoxycarbonylamino-[5-((S)-2-carbamoyl-propyl)-2,4-dinitro-phenylamino]-acetic acid
  参考文献：
  名称：

  (R)-tert-Butoxycarbonylamino-fluorenylmethoxycarbonyl-glycine from (S)-Benzyloxycarbonyl-serine or from Papain Resolution of the Corresponding Amide or Methyl Ester

  摘要：

  The enantiospecific synthesis of (R)-Boc-(Fmoc)-aminoglycine 7 was achieved. (S)-Cbz-serine 1 was reacted with diphenylphosphoryl azide in the presence of triethylamine to yield cyclic (S) carbamate 2. The ring nitrogen of 2 was protected with a Boc group (3). The cyclic carbamate of 3, was hydrolyzed with benzyltrimethylammonium hydroxide to yield the (R)-enantiomer of alcohol. The oxidation of 4 with pyridinium dichromate yielded the enantiomerically pure (87% ee) (R)Boc-(Cbz)-aminoglycine 5, which was converted to 7 with retention of optical purity. Similarly, starting from (S)-Boc-serine 9, cyclic (S) carbamate 10 was obtained. The ring nitrogen of 10 was protected with a Cbz group (11) with retention of configuration. The cyclic carbamate of 11 was base hydrolyzed to yield 12, the (S)-enantiomer alcohol. Independently Boc-(Fmoc)-aminoglycine amide 13 and BoC-(Fmoc)-aminoglycine methyl ester 14 were resolved using papain. The stereochemistry of the isolated acid was determined to be (R) by coelution an HPLC of its. derivative, : with Marfey's reagent and that of-an authentic sample (7) obtained by enantiospecific synthesis.

  DOI：

  10.1021/jo000736e
• 作为产物：
  描述：

  N-Boc-N′-Fmoc-二氨基乙酸 在 水 、 potassium carbonate 、 papain 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.17h， 生成 (R)-tert-butoxycarbonylamino-fluorenylmethoxycarbonylaminoacetic acid
  参考文献：
  名称：

  (R)-tert-Butoxycarbonylamino-fluorenylmethoxycarbonyl-glycine from (S)-Benzyloxycarbonyl-serine or from Papain Resolution of the Corresponding Amide or Methyl Ester

  摘要：

  The enantiospecific synthesis of (R)-Boc-(Fmoc)-aminoglycine 7 was achieved. (S)-Cbz-serine 1 was reacted with diphenylphosphoryl azide in the presence of triethylamine to yield cyclic (S) carbamate 2. The ring nitrogen of 2 was protected with a Boc group (3). The cyclic carbamate of 3, was hydrolyzed with benzyltrimethylammonium hydroxide to yield the (R)-enantiomer of alcohol. The oxidation of 4 with pyridinium dichromate yielded the enantiomerically pure (87% ee) (R)Boc-(Cbz)-aminoglycine 5, which was converted to 7 with retention of optical purity. Similarly, starting from (S)-Boc-serine 9, cyclic (S) carbamate 10 was obtained. The ring nitrogen of 10 was protected with a Cbz group (11) with retention of configuration. The cyclic carbamate of 11 was base hydrolyzed to yield 12, the (S)-enantiomer alcohol. Independently Boc-(Fmoc)-aminoglycine amide 13 and BoC-(Fmoc)-aminoglycine methyl ester 14 were resolved using papain. The stereochemistry of the isolated acid was determined to be (R) by coelution an HPLC of its. derivative, : with Marfey's reagent and that of-an authentic sample (7) obtained by enantiospecific synthesis.

  DOI：

  10.1021/jo000736e

文献信息

• Structure-based design of α-amido aldehyde containing gluten peptide analogues as modulators of HLA-DQ2 and transglutaminase 2
  作者：Matthew Siegel、Jiang Xia、Chaitan Khosla

  DOI：10.1016/j.bmc.2007.06.020

  日期：2007.9

  Complete, life-long exclusion of gluten containing foods from the diet is the only available treatment for celiac sprue, a widespread immune disease of the small intestine. Investigations into the molecular pathogenesis of celiac sprue have identified the major histocompatibility complex protein HLA-DQ2 and the multi-functional enzyme transglutaminase 2 as potential pharmacological targets. Based upon the crystal structure of HLA-DQ2, we rationally designed an aldehyde-functionalized, gluten peptide analogue as a tight-binding HLA-DQ2 ligand. Aldehyde-bearing gluten peptide analogues were also designed as high-affinity, reversible inhibitors of transglutaminase 2. By varying the side-chain length of the aldehyde-functionalized amino acid, we found that the optimal transglutaininase 2 inhibitor was 5 methylene units in length, 2 carbon atoms longer than its natural glutamine substrate. (c) 2007 Elsevier Ltd. All rights reserved.
• (<i>R</i>)-<i>tert</i>-Butoxycarbonylamino-fluorenylmethoxycarbonyl-glycine from (<i>S</i>)-Benzyloxycarbonyl-serine or from Papain Resolution of the Corresponding Amide or Methyl Ester
  作者：Michal Sypniewski、Botond Penke、Lajos Simon、Jean Rivier

  DOI：10.1021/jo000736e

  日期：2000.10.1

  The enantiospecific synthesis of (R)-Boc-(Fmoc)-aminoglycine 7 was achieved. (S)-Cbz-serine 1 was reacted with diphenylphosphoryl azide in the presence of triethylamine to yield cyclic (S) carbamate 2. The ring nitrogen of 2 was protected with a Boc group (3). The cyclic carbamate of 3, was hydrolyzed with benzyltrimethylammonium hydroxide to yield the (R)-enantiomer of alcohol. The oxidation of 4 with pyridinium dichromate yielded the enantiomerically pure (87% ee) (R)Boc-(Cbz)-aminoglycine 5, which was converted to 7 with retention of optical purity. Similarly, starting from (S)-Boc-serine 9, cyclic (S) carbamate 10 was obtained. The ring nitrogen of 10 was protected with a Cbz group (11) with retention of configuration. The cyclic carbamate of 11 was base hydrolyzed to yield 12, the (S)-enantiomer alcohol. Independently Boc-(Fmoc)-aminoglycine amide 13 and BoC-(Fmoc)-aminoglycine methyl ester 14 were resolved using papain. The stereochemistry of the isolated acid was determined to be (R) by coelution an HPLC of its. derivative, : with Marfey's reagent and that of-an authentic sample (7) obtained by enantiospecific synthesis.