3'-O-ethylthymidine | 81542-72-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-ethylthymidine
• 英文别名: Thymidine, 3'-O-ethyl-；1-[(2R,4S,5R)-4-ethoxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 81542-72-5
• 化学式: C₁₂H₁₈N₂O₅
• 分子量: 270.285
• InChiKey: KXGTYHLMWACQAG-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-O-ethylthymidine 在 吡啶 、 草酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 5'-deoxy-5',5'-(N,N'-diphenylethylenediamino)-3'-O-ethylthymidine
  参考文献：
  名称：

  Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-O-Ethyl-4′-C-(hydroxymethyl)thymidine: Introduction of a Novel Class of Phosphodiester Internucleoside Linkages

  摘要：

  3'-O-Ethyl-4'-C-(hydroxymethyl)thymidine (5) was synthesized and converted into the phosphoramidite building block 8. Novel oligodeoxynucleotide analogues containing 4'-C-hydroxymethyl phosphodiester internucleoside linkages were synthesized on an automated DNA-synthesizer. The hybridization properties and enzymatic stability were studied on oligomers with one to four modifications. The 3'-end modified oligodeoxynucleotides were resistent towards 3'-exonuclease degradation and showed only moderate lowered affinity towards complementary DNA compared with oligodeoxynucleotides bearing modifications in the middle.

  DOI：

  10.1080/15257779408010674
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 氢氧化钾 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 11.0h， 生成 3'-O-ethylthymidine
  参考文献：
  名称：

  Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-O-Ethyl-4′-C-(hydroxymethyl)thymidine: Introduction of a Novel Class of Phosphodiester Internucleoside Linkages

  摘要：

  3'-O-Ethyl-4'-C-(hydroxymethyl)thymidine (5) was synthesized and converted into the phosphoramidite building block 8. Novel oligodeoxynucleotide analogues containing 4'-C-hydroxymethyl phosphodiester internucleoside linkages were synthesized on an automated DNA-synthesizer. The hybridization properties and enzymatic stability were studied on oligomers with one to four modifications. The 3'-end modified oligodeoxynucleotides were resistent towards 3'-exonuclease degradation and showed only moderate lowered affinity towards complementary DNA compared with oligodeoxynucleotides bearing modifications in the middle.

  DOI：

  10.1080/15257779408010674

文献信息

• Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes
  作者：Alexander Hampton、Ram R. Chawla、Francis Kappler

  DOI：10.1021/jm00348a007

  日期：1982.6

  eight positions of thymidine (TdR) have been examined as inhibitors of rat mitochondrial (M-TK) and cytoplasmic (C-TK) isozymes of thymidine kinase. A C-TK (pI = 7.5) and an M-TK (pI = 5.1) from rat spleen were purified to apparent isozymic homogeneity by isoelectric focusing. Affinities relative to that of TdR for the TdR sites of the isozymes were derived by dividing the Michaelis constants of TdR

  通过对胸苷（TdR）的八个位置上的基团进行单次替换或置换获得的衍生物已作为大鼠线粒体（M-TK）和胸苷激酶胞质（C-TK）同工酶的抑制剂进行了研究。通过等电聚焦将大鼠脾脏的C-TK（pI = 7.5）和M-TK（pI = 5.1）纯化为明显的同功同质性。通过将TdR的米氏常数除以抑制常数，可得出相对于TdR同工酶的TdR位点的亲和力。在八种TdR衍生物中，五种对M-TK位点具有更高的亲和力，另外两种对C-TK位点具有更高的亲和力。最有效和/或选择性的抑制剂是3'-O-苄基-TdR（相对于TdR，相对于M-TK的亲和力为100％；相对于C-TK相对于M-TK的亲和力为7.5），5-氨基-2 '-脱氧尿苷（对M-TK的相对亲和力，11％; 对M-TK的差分亲和力为26），5'-氨基-5'-脱氧TdR（对C-TK的相对亲和力为67％;对C-TK的差分亲和力大于25）。修饰某些取代基的效果表明，这
• MCGUIGAN, C.;NICHOLLS, S. R.;OCONNOR, T. J.;KINCHINGTON, D., ANTIVIRAL CHEM. AND CHEMOTHER., 1,(1990) N, C. 25-33
  作者：MCGUIGAN, C.、NICHOLLS, S. R.、OCONNOR, T. J.、KINCHINGTON, D.

  DOI：——

  日期：——
• METHODS OF SCREENING FOR NUCLEOSIDE ANALOGS THAT ARE INCORPORATED BY HIV REVERSE TRANSCRIPTASE AND CAUSE INCORRECT BASE PAIRING
  申请人：DARWIN MOLECULAR CORPORATION

  公开号：EP0767842A1

  公开（公告）日：1997-04-16
• [EN] METHODS OF SCREENING FOR NUCLEOSIDE ANALOGS THAT ARE INCORPORATED BY HIV REVERSE TRANSCRIPTASE AND CAUSE INCORRECT BASE PAIRING<br/>[FR] PROCEDES DE CRIBLAGE D'ANALOGUES DE NUCLEOSIDES INCORPORES PAR LA TRANSCRIPTASE INVERSE DU VIH ET PROVOQUANT UN APPARIEMENT INCORRECT ENTRE BASES
  申请人：LOEB, Lawrence, A.

  公开号：WO1996000797A1

  公开（公告）日：1996-01-11

  (EN) Methods and compositions related to HIV are disclosed. Using the methods of the present invention, nucleoside analogs may be screened for the ability to be incorporated by reverse transcriptase of human immunodeficiency virus ('HIV RT') and cause incorrect base pairing. Progressive mutation of the virus by such nucleoside analogs renders it non-viable.(FR) L'invention concerne des procédés et des compositions relatifs au VIH. Selon les procédés de l'invention, on peut cribler des analogues de nucléosides afin de déterminer leur capacité à être incorporés par la transcriptase inverse du virus d'immunodéficience humaine et provoquer un appariement incorrect entre bases. La mutation progressive du virus induite par de tels analogues de nucléosides permet de le rendre non viable.
• [EN] METHOD FOR AMPLIFYING UNKNOWN DNA SEQUENCE ADJACENT TO KNOWN SEQUENCE<br/>[FR] PROCEDE PERMETTANT D'AMPLIFIER UNE SEQUENCE D'ADN INCONNUE ADJACENTE A UNE SEQUENCE CONNUE
  申请人：SEEGENE INC

  公开号：WO2005045073A1

  公开（公告）日：2005-05-19

  The present invention relates to a method for amplifying an unknown nucleotide sequence adjacent to a known nucleotide sequence, which comprises the step of (a) performing a primary amplification of said unknown nucleotide sequence using a DNA walking annealing control primer (DW-ACP) and a first target-specific primer; in which said step (a) comprises: (a-1) performing a first-stage amplification of said unknown nucleotide sequence at a first annealing temperature, comprising at least one cycle of primer annealing, primer extending and denaturing using a first degenerate DW-ACP containing a degenerate random nucleotide sequence to hybridize with said unknown nucleotide sequence and a hybridizing nucleotide sequence substantially complementary to a site on said unknown nucleotide sequence; and (a-2) performing a second-stage amplification at a second annealing temperature to render said first degenerate DW-ACP not to function as a primer.