N²-Phenylacetyl-2'-deoxyguanosine | 92447-25-1

• 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: N²-Phenylacetyl-2'-deoxyguanosine
• 英文别名: 2-N-(phenylacetyl)-2'-deoxyguanosine；2-N-phenylacetyl-2'-deoxyguanosine；N-(9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenylacetamide；N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-phenylacetamide
• CAS: 92447-25-1
• 化学式: C₁₈H₁₉N₅O₅
• 分子量: 385.379
• InChiKey: DGSXFEJDMIOLCB-OUCADQQQSA-N

物化性质

• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-Phenylacetyl-2'-deoxyguanosine 在 吡啶 、 bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride 、 N,N-二异丙基乙胺 、 3-硝基-1,2,4-三氮唑 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 22.0h， 生成 tributylammonium 5'-O-dimethoxytrityl-O⁶-diphenylcarbamoyl-N²-phenylacetyl-2'-deoxyguanosin-3'-yl methyl boranophosphate
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 吡啶 、 ammonium hydroxide 、 1-羟基苯并三唑 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 0.75h， 生成 N²-Phenylacetyl-2'-deoxyguanosine
  参考文献：
  名称：

  An Improved Procedure for the Protection of 2′-Deoxyguanosine

  摘要：

  N 2-苯乙酰基-2′-脱氧鸟苷的制备方法是：用 1-羟基苯并三唑预处理苯乙酰氯，然后将所形成的加合物加入 2′-脱氧鸟苷的三[三甲基硅]醚衍生物中，可获得高产率和高纯度的 2′-脱氧鸟苷。随后，用 9-氯-9-苯基氧杂蒽处理结晶产物，可得到适用于寡脱氧核苷酸合成过程的结晶物质。

  DOI：

  10.1055/s-1986-31471

文献信息

• Chemoenzymatic Synthesis of Nucleopeptides
  作者：Stefanie Flohr、Volker Jungmann、Herbert Waldmann

  DOI：10.1002/(sici)1521-3765(19990201)5:2<669::aid-chem669>3.0.co;2-v

  日期：1999.2.1

  Nucleoproteins, in which the hydroxy group of a serine, a threonine, or a tyrosine, is linked through a phosphodiester group to the 3'- or 5'-end of DNA or RNA, play decisive roles in important biological processes. They may even have a major part in the process of viral replication by nucleoprotein-primed elongation of the oligonucleotide strand. For the study of the biological phenomena, in which nucleoproteins are involved, nucleopeptides with the characteristic linkage between the peptide chain and the oligonucleotide of their parent nucleoproteins may serve as powerful tools. However, the synthesis of these compounds is complicated by their pronounced acid- and base-lability, as well as their multifunctionality. As a result, protecting groups, which can be removed under the mildest conditions, are required. For the construction of such peptide conjugates using a flexible building block strategy, a combination of enzyme-labile and chemical protecting groups was developed. The C-terminal blocking function can be removed selectively from fully protected nucleoamino acid methyl, 2-methoxyethyl (ME), and methoxyethoxyethyl (MEE) esters by saponification of the esters. After elongation of the peptide chain with amino acid or peptide methyl, ME, MEE, and choline esters, the C-terminal ester blocking group can again be removed easily. The methyl, ME, and MEE esters are cleaved off with lipase, and the choline ester group is selectively attacked by butyrylcholine esterase. The nucleoamino acids and peptides formed may be fully deprotected. To this end, the enzyme-labile N-phenylacetyl (PhAc) group, which was employed to mask the amino functions of the nucleobases, was removed. The O-acetate in the deoxyribose was saponified, and the allyl protecting groups present were cleaved by Pd-0-mediated allyl transfer. By combination of these techniques, a nucleopeptide was produced, which represents the characteristic linkage region of the nucleoprotein of adenovions 2. The conditions, under which the enzymatic deprotections proceed, are so mild that no undesired side reaction is observed, that is no depurination or beta elimination of the nucleosides occurs. In addition, the specificity of the biocatalysts ensures that the peptide bonds and the other protecting groups present are not attacked either.
• Reese, Colin B.; Skone, Philip A., Journal of the Chemical Society. Perkin transactions I, 1984, p. 1263 - 1271
  作者：Reese, Colin B.、Skone, Philip A.

  DOI：——

  日期：——
• Balgobin, Neil; Josephson, Staffan; Chattopadhyaya, Jyoti B., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 201 - 212
  作者：Balgobin, Neil、Josephson, Staffan、Chattopadhyaya, Jyoti B.

  DOI：——

  日期：——
• Chemoenzymic Synthesis of P^α-Methyl Deoxynucleoside Triphosphates
  作者：Magda A. Dineva、Dimiter D. Petkov

  DOI：10.1080/07328319608002447

  日期：1996.9

  5'-O-(methylphosphonyl)-N-(phenylacetyl)-2'-deoxycytidine, deoxyadenosine and deoxyguanosine were pyrophosphorylated and the resulting N-protected P-alpha-methyl nucleoside triphosphates were deblocked by treatment with penicillin amidase at pH 7.8, 25 degrees C to give P-alpha-methyl nucleoside triphosphates.
• The Phenylacetyl Group—The First Amino Protecting Group That Can Be Removed Enzymatically from Oligonucleotides in Solution and on a Solid Support
  作者：Herbert Waldmann、Armin Reidel

  DOI：10.1002/anie.199706471

  日期：1997.4.4

  Penicillin G acylase from E. coli was used to cleave the phenylacetyl group—the first enzyme‐labile protecting group for the amino function of nucleobases. Now protected oligonucleotides can be unmasked both in solution and on solid supports with this versatile enyzme under mild conditions (pH 7, room temperature). These results may lead to the development of new enzymatic reactions in oligonucleotide and solid‐phase chemistry as well as in combinatorial chemistry.