1'N-（4,4'-二甲氧基三苯甲基）生物素 | 144095-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 1'N-（4,4'-二甲氧基三苯甲基）生物素
• 英文名称: N¹-4,4'-dimethoxytrityl-(+)-biotin
• 英文别名: 1-N-(4,4'-dimethoxytrityl)-D-(+)-biotin；D-biotin；DMT-Biotin；5-[(3aR,6S,6aS)-3-[bis(4-methoxyphenyl)-phenylmethyl]-2-oxo-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-6-yl]pentanoic acid
• CAS: 144095-63-6
• 化学式: C₃₁H₃₄N₂O₅S
• 分子量: 546.687
• InChiKey: RMWVJZXKPGLZEJ-YCVJPRETSA-N

物化性质

• 沸点：
  799.6±60.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)
• 溶解度：
  二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1'N-（4,4'-二甲氧基三苯甲基）生物素 在 吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 6-(1-N-(4,4'-dimethoxytrityl)-D-(+)-biotinoyl)aminohexanoic acid
  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：

  D-生物素甲酯 在 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 1'N-（4,4'-二甲氧基三苯甲基）生物素
  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

• [EN] CYSTEINE ARYLATION DIRECTED BY A GENETICALLY ENCODABLE π-CLAMP<br/>[FR] ARYLATION DE CYSTÉINE DIRIGÉE PAR UN N-CLAMP ENCODABLE GÉNÉTIQUEMENT
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2015175941A1

  公开（公告）日：2015-11-19

  Disclosed are methods of single-site-specific cysteine modification on peptide/protein molecules under physiologically relevant conditions. This process features several significant advantages over existing methods of peptide modification, such as specificity towards thiols over other nucleophiles (e.g., amines, hydroxyls), excellent functional group tolerance, and mild reaction conditions. Especially important is the specificity observed for thiols appearing in an X-Cys-Pro-X sequence over other thiols or disulfides, where X is Phe, Trp, or Tyr; under the inventive conditions, other cysteines or reactive functional groups on the same peptide/protein chain are not functionalized.

  披露了在生理条件下对肽/蛋白分子进行单位点特异性半胱氨酸修饰的方法。该过程具有几个显著优点，相比现有的肽修饰方法，如对硫醇具有特异性而不影响其他亲核试剂（如胺基、羟基）、良好的官能团容忍性和温和的反应条件。尤其重要的是，观察到对出现在X-Cys-Pro-X序列中的硫醇的特异性，而不影响其他硫醇或二硫键，其中X为Phe、Trp或Tyr；在创新的条件下，同一肽/蛋白链上的其他半胱氨酸或反应性官能团不会发生功能化。
• 长链生物素标记物及其制备方法和用途
  申请人：伯科生物医学科技（北京）有限公司

  公开号：CN109134541B

  公开（公告）日：2020-10-27

  本发明公开长链生物素标记物及其制备方法和用途。本发明的长链生物素标记物包括生物素分子、间隔臂和反应基团。其中，生物素分子包括环状结构和戊酸侧链，间隔臂具有式(I)所示的结构，反应基团具有式(II)所示的结构，生物素分子中的戊酸侧链与间隔臂第一末端的NH连接，间隔臂的第二末端的氧与反应基团的磷结合形成O‑P键，从而将间隔臂与反应基团连接。本发明的长链生物标记物可用于基因的捕获测序。‑NH(CH2)mO‑(‑C＝O‑NH‑(CH2‑CH2O‑)4)n式(I)
• Biotin and fluorescein labeling of biomolecules by active esters of 1-phenylpyrazolin-5-ones
  作者：Jonathan N. Kremsky、Malcolm Pluskal、Shelagh Casey、Heather Perry-O'Keefe、Steven A. Kates、Nanda D. Sinha

  DOI：10.1016/0040-4039(96)00833-7

  日期：1996.6

  The synthesis of 1-phenylpyrazolin-5-one carboxylate esters of biotin and fluorescein and their specific reactivity with amines under mild conditions to label various synthetic biopolymers such as oligonucleotides, peptides and PNA's is described.

  描述了生物素和荧光素的1-苯基吡唑啉-5-酮羧酸酯的合成及其在温和条件下与胺的比反应性，以标记各种合成的生物聚合物，例如寡核苷酸，肽和PNA。
• Synthesis of a biotin-conjugate of phosmidosine O-ethyl ester as a G1 arrest antitumor drug
  作者：Mitsuo Sekine、Kazuhisa Okada、Kohji Seio、Tohru Obata、Takuma Sasaki、Hideaki Kakeya、Hiroyuki Osada

  DOI：10.1016/j.bmc.2004.09.037

  日期：2004.12

  This paper deals with the synthesis of a stable biotin-phosmidosine conjugate molecule 3 that is required for isolation of biomolecules that bind to phosmidosine (1). It was found that introduction of a biotin residue into the 6-N position of phosmidosine could be carried out by reaction of an N-7-Boc-7,8-dihydro-8-oxoadenosine derivative 13 with phenyl chloroformate followed by displacement with a diamine derivative 6 along with the simultaneous removal of the Boc group and one of the two phenoxycarbonyl groups and the successive condensation with an N-tritylated biotin derivative 5. The condensation of an N-prolylphosphorodiamidite derivative 4 with an appropriately protected 7,8-dihydro-8-oxoadenosine derivative 17 having the biotin residue gave the coupling product 18, which was deprotected to give the biotin-phosmidosine (O-ethyl ester) conjugate 3. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.