4(S)-amino-1,2-(R and S)-pentanediol | 381718-60-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4(S)-amino-1,2-(R and S)-pentanediol
• 英文别名: (4S)-4-aminopentane-1,2-diol
• CAS: 381718-60-1
• 化学式: C₅H₁₃NO₂
• 分子量: 119.164
• InChiKey: YFBHVTQPFSQXFB-ROLXFIACSA-N

物化性质

• 沸点：
  263.5±25.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-[2-氟-6-(2-三甲基硅烷基乙氧基)嘌呤-9-基]-2-(羟基甲基)四氢呋喃-3-醇 、 4(S)-amino-1,2-(R and S)-pentanediol 在 N,N-二异丙基乙胺 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以78%的产率得到N2-(1(S)-methyl-3(R and S),4-dihydroxybutyl)deoxyguanosine
  参考文献：
  名称：

  Stereospecific Synthesis of Oligonucleotides Containing Crotonaldehyde Adducts of Deoxyguanosine

  摘要：

  Crotonaldehyde reacts with DNA to form two diastereomeric 1,N-2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The resulting N-2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.

  DOI：

  10.1021/tx0100690
• 作为产物：
  描述：

  (S)-3-(benzoylamino)-4-pentene 在 盐酸 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 4(S)-amino-1,2-(R and S)-pentanediol
  参考文献：
  名称：

  Stereospecific Synthesis of Oligonucleotides Containing Crotonaldehyde Adducts of Deoxyguanosine

  摘要：

  Crotonaldehyde reacts with DNA to form two diastereomeric 1,N-2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The resulting N-2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.

  DOI：

  10.1021/tx0100690

文献信息

• Stereospecific Synthesis of Oligonucleotides Containing Crotonaldehyde Adducts of Deoxyguanosine
  作者：Lubomir V. Nechev、Ivan Kozekov、Constance M. Harris、Thomas M. Harris

  DOI：10.1021/tx0100690

  日期：2001.11.1

  Crotonaldehyde reacts with DNA to form two diastereomeric 1,N-2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The resulting N-2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O-6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.