2'-O-(bis(2-methoxyethoxy)methyl)-6-N-(4,4'-dimethoxytrityl)-3'-O-(N-(6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoyl)-L-phenylalanyl)adenosine | 874889-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-O-(bis(2-methoxyethoxy)methyl)-6-N-(4,4'-dimethoxytrityl)-3'-O-(N-(6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoyl)-L-phenylalanyl)adenosine
• 英文别名: [(2R,3R,4R,5R)-4-[bis(2-methoxyethoxy)methoxy]-5-[6-[[bis(4-methoxyphenyl)-phenylmethyl]amino]purin-9-yl]-2-(hydroxymethyl)oxolan-3-yl] (2S)-2-[6-[5-[(3aR,6S,6aS)-3-[bis(4-methoxyphenyl)-phenylmethyl]-2-oxo-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-6-yl]pentanoylamino]hexanoylamino]-3-phenylpropanoate
• CAS: 874889-95-9
• 化学式: C₈₄H₉₇N₉O₁₆S
• 分子量: 1520.81
• InChiKey: ATOGALWJLAWLEZ-PWLRJTMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  110
• 可旋转键数：
  42
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  310
• 氢给体数：
  5
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  2'-O-(bis(2-acetoxyethoxy)methyl)-5'-O-[bis(trimethylsiloxy)(cyclododecyloxy)silyl]-4-N-(4,4'-dimethoxytrityl)cytidine 3'-(N,N-diisopropyl)methoxyphosphoramidite 、 2'-O-(bis(2-methoxyethoxy)methyl)-6-N-(4,4'-dimethoxytrityl)-3'-O-(N-(6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoyl)-L-phenylalanyl)adenosine 在 4 A molecular sieve 、 PhlmOTf 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.7h， 生成
  参考文献：
  名称：

  Synthesis of the Ribosomal P-Site Substrate CCA-pcb

  摘要：

  CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both X-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.

  DOI：

  10.1021/ol052484f
• 作为产物：
  描述：

  在 四甲基乙二胺 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以84%的产率得到2'-O-(bis(2-methoxyethoxy)methyl)-6-N-(4,4'-dimethoxytrityl)-3'-O-(N-(6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoyl)-L-phenylalanyl)adenosine
  参考文献：
  名称：

  Synthesis of the Ribosomal P-Site Substrate CCA-pcb

  摘要：

  CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both X-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.

  DOI：

  10.1021/ol052484f

文献信息

• Synthesis of Isotopically Labeled P-Site Substrates for the Ribosomal Peptidyl Transferase Reaction
  作者：Minghong Zhong、Scott A. Strobel

  DOI：10.1021/jo702070m

  日期：2008.1.1

  (cytidine), 93% for 2‘/3‘-18O (adenosine), and 64% for 1-18O (Phe). A new synthesis of highly enriched [1-18O2]phenylalanine has been developed. The synthesis of [3‘-18O]adenosine was improved by Lewis acid aided regioselective ring opening of the epoxide and by an economical SN2−SN2 method with high isotopic enrichment (93%). Such substrates are valuable for studies of the ribosomal peptidyl transferase reaction

  核糖体 P 位点底物的同位素异构体，即三核苷酸肽偶联物 CCA-pcb（Zhong, M.；Strobel, SA Org. Lett. 2006 , 8 , 55-58），已通过 26-35 个步骤设计和合成。这些包括氨基酸的 α-氢、羰基碳和羰基氧、腺苷的 O2' 和 O3' 处的单个同位素取代，以及两个胞苷的 N3 和 N4 中的远程标记。这些同位素是通过将胞苷酰-(3',5')-胞苷亚磷酰胺同位素作为常见的合成中间体与同位素取代的 A-Phe-cap-生物素 (A-pcb) 偶联来合成的。1- 13 C (Phe)、2- 2 H (Phe) 和 3,4- 15 N 2的同位素富集率高于 99%(胞苷)，2'/3'- 18 O (腺苷)为 93% ，1- 18 O (Phe)为 64% 。已开发出一种高富集 [1- 18 O 2 ] 苯丙氨酸的新合成方法。[3'- 18 O]腺苷的合
• Synthesis of the Ribosomal P-Site Substrate CCA-pcb
  作者：Minghong Zhong、Scott A. Strobel

  DOI：10.1021/ol052484f

  日期：2006.1.1

  CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both X-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.