3'-L-(p-methoxyphenylalanylamino)-3'-deoxy-β-D-adenosine | 71508-05-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3'-L-(p-methoxyphenylalanylamino)-3'-deoxy-β-D-adenosine
• 英文别名: 3'-L-(O-methyl)tyrosylamino-3'-deoxy-β-D-adenosine；3'-(p-methoxy-L-phenylalanyl)amino-3'-deoxyadenosine；3'-(O-methyl-L-tyrosyl)amido-3'-deoxyadenosine；3'-[O-methyl-L-tyrosyl]amido-3'-deoxyadenosine；3'-deoxy-3'-L-(O-methyltyrosyl)amino-adenosine；puromycin；3'-Deoxy-3'-[(O-Methyl-L-Tyrosyl)amino]adenosine；(2S)-2-amino-N-[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
• CAS: 71508-05-9
• 化学式: C₂₀H₂₅N₇O₅
• 分子量: 443.462
• InChiKey: FEUXXQHFLIJGOX-GJIZYBQMSA-N

物化性质

• 熔点：
  128-133 °C
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  184
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-L-(p-methoxyphenylalanylamino)-3'-deoxy-β-D-adenosine 在 phosphate buffer 作用下， 反应 5.0h， 以99%的产率得到3'-(O-methyl-L-tyrosyl)amido-3'-deoxyinosine
  参考文献：
  名称：

  Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase

  摘要：

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.

  DOI：

  10.1021/ol070818q
• 作为产物：
  描述：

  腺苷 在 吡啶 、 氟化铵 、 二甲基溴化硼 、 2-乙酰氧基异丁酰溴 、 sodium hydride 、 三乙胺 、 甲胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 69.08h， 生成 3'-L-(p-methoxyphenylalanylamino)-3'-deoxy-β-D-adenosine
  参考文献：
  名称：

  使用改良的Robins方法合成嘌呤霉素类似物的最短合成路线

  摘要：

  我们报告了商业化的异氰酸乙烯基酯在七个步骤中从腺苷到N 6-双-去甲基嘌呤霉素的实用合成路线的实用性，总收率达65％。该合成途径的主要特征是将3'-溴-2'-氨基甲酰基衍生物8干净地一锅转化为3'-氨基-3'-脱氧腺苷衍生物10。迄今为止，该合成是向3'-（氨基酰氨基）脱氧腺苷最短的合成途径。

  DOI：

  10.1021/jo102178h

文献信息

• A Practical Route to 3‘-Amino-3‘-deoxyadenosine Derivatives and Puromycin Analogues
  作者：Nhat Quang Nguyen-Trung、Oliver Botta、Silvia Terenzi、Peter Strazewski

  DOI：10.1021/jo026627c

  日期：2003.3.1

  3'-aminoacylamino-3'-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3'-azido derivative 10 was obtained through a 3'-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation step using the Garegg reagent. The coupling reaction between an Fmoc-l-amino acid and the fully protected

  3'-氨基酰基氨基-3'-脱氧腺苷是抗生素嘌呤霉素的类似物，是由腺苷合成的。它们的关键3'-叠氮基衍生物10是通过3'-氧化/还原/取代过程获得的。使用Garegg试剂为氧化步骤开发了大规模的改良纯化方案。Fmoc-1-氨基酸与3'-氨基-3'-脱氧腺苷11的完全保护形式之间的偶联反应以高收率提供了氨基酰化的化合物12。嘌呤霉素类似物以10个步骤获得，总产率高达23％（14c）。
• Shorter puromycin analog synthesis by means of an efficient Staudinger–Vilarrasa coupling
  作者：Hubert Chapuis、Peter Strazewski

  DOI：10.1016/j.tet.2006.09.045

  日期：2006.12

  An efficient Staudinger–Vilarrasa coupling generates amides from azides and 1-hydroxybenzotriazole esters of amino- or hydroxy acid derivatives in very high isolated yields and purity. New puromycin analogs, mostly putative biosynthetic intermediates, were synthesized in nine steps from adenosine.

  有效的Staudinger-Vilarrasa偶联可从叠氮化物和氨基或羟基酸衍生物的1-羟基苯并三唑酯生成酰胺，分离产率和纯度很高。新的嘌呤霉素类似物（主要是假定的生物合成中间体）是从腺苷经九步合成的。
• High-Yield Immobilization of a Puromycin Analogue for the Solid Support Synthesis of Aminoacyl-tRNA Fragments
  作者：Nhat Quang Nguyen-Trung、Silvia Terenzi、Gerd Scherer、Peter Strazewski

  DOI：10.1021/ol0346638

  日期：2003.7.1

  [GRAPHICS]An efficient procedure for the immobilization of 3'-deoxy-3'-(O-methyltyrosyl)aminoadenosine was developed. A poly(ethylene glycol)-derived diacid linker/spacer was attached to aminomethyl polystyrene. Coupling of the 2'-hydroxy instead of the 2'-O-succinylated ribonucleoside resulted in high immmobilization yields (over 80%) and allowed for the recovery of valuable unreacted material. This specific procedure should be applicable to other ribonucleosides containing a bulky modification at the 3'-position and can be used for the stepwise construction of 3'-aminoacyl- or 3'-peptidyl-RNA conjugates.
• The Shortest Synthetic Route to Puromycin Analogues Using a Modified Robins Approach
  作者：Kollappillil S. Krishnakumar、Sébastien Goudedranche、Denis Bouchu、Peter Strazewski

  DOI：10.1021/jo102178h

  日期：2011.4.1

  of commercial vinyl isocyanate for a practical synthetic route from adenosine to N6-bis-demethylpuromycin in seven steps and 65% overall yield. A clean one-pot conversion of 3′-bromo-2′-carbamoyl derivative 8 to 3′-amino-3′-deoxyadenosine derivative 10 is the main feature of this synthetic pathway. This synthesis is the shortest synthetic route toward 3′-(aminoacylamido)deoxyadenosines to date.

  我们报告了商业化的异氰酸乙烯基酯在七个步骤中从腺苷到N 6-双-去甲基嘌呤霉素的实用合成路线的实用性，总收率达65％。该合成途径的主要特征是将3'-溴-2'-氨基甲酰基衍生物8干净地一锅转化为3'-氨基-3'-脱氧腺苷衍生物10。迄今为止，该合成是向3'-（氨基酰氨基）脱氧腺苷最短的合成途径。
• Facile and Rapid Access to Inosine Puromycin Analogues through the Use of Adenylate Deaminase
  作者：Adib Charafeddine、Hubert Chapuis、Peter Strazewski

  DOI：10.1021/ol070818q

  日期：2007.7.1

  To study the ribosomal peptidyl transfer, puromycin analogues are of interest in which adenine has been replaced by hypoxanthine. We synthesized inosine puromycin analogues from 3'-azidodeoxyadenosine derivatives using adenylate deaminase for the quantitative transformation of the N-heterocycle. The amino acid coupling was carried out under Staudinger-Vilarrasa conditions in 94% yield starting from the protected and in 82% using the unprotected azide, thus, in the presence of two hydroxyls and a lactam function.