4-[4-(tert-butoxycarbonylamino)butanamido]but-2-ynyl-4-nitrobenzenesulfonate | 912477-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-(tert-butoxycarbonylamino)butanamido]but-2-ynyl-4-nitrobenzenesulfonate
• 英文别名: 4-[4-[(2-Methylpropan-2-yl)oxycarbonylamino]butanoylamino]but-2-ynyl 4-nitrobenzenesulfonate；4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoylamino]but-2-ynyl 4-nitrobenzenesulfonate
• CAS: 912477-40-8
• 化学式: C₁₉H₂₅N₃O₈S
• 分子量: 455.489
• InChiKey: RORKEWMXNNHZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[4-(tert-butoxycarbonylamino)butanamido]but-2-ynyl-4-nitrobenzenesulfonate 在 甲酸 、 溶剂黄146 、 三氟乙酸 作用下， 反应 9.0h， 生成 5'-[(S)-[(3S)-3-amino-3-carboxypropyl]-4-[4-aminobutanamido]but-2-ynylsulfonio]-5'-deoxyadenosine
  参考文献：
  名称：

  Targeted Labeling of DNA by Methyltransferase-Directed Transfer of Activated Groups (mTAG)

  摘要：

  Methyltransferases catalyze highly specific transfers of methyl groups from the ubiquitous cofactor S-adenosyl-L-methionine (AdoMet) to various biopolymers like DNA, RNA, and proteins. Here we describe the first synthetic analogue of AdoMet with an activated side chain carrying a primary amino group that permits efficient methyltransferase-directed functionalization of DNA and subsequent amine-specific chemoligations with various reporter groups. The demonstrated two-step sequence-specific labeling of natural DNA offers a facile way to query the methylation status of the target sites and envisions numerous applications in functional studies and medical diagnostics.

  DOI：

  10.1021/ja0691876
• 作为产物：
  描述：

  N-BOC-GAMMA-氨基丁酸 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-[4-(tert-butoxycarbonylamino)butanamido]but-2-ynyl-4-nitrobenzenesulfonate
  参考文献：
  名称：

  Targeted Labeling of DNA by Methyltransferase-Directed Transfer of Activated Groups (mTAG)

  摘要：

  Methyltransferases catalyze highly specific transfers of methyl groups from the ubiquitous cofactor S-adenosyl-L-methionine (AdoMet) to various biopolymers like DNA, RNA, and proteins. Here we describe the first synthetic analogue of AdoMet with an activated side chain carrying a primary amino group that permits efficient methyltransferase-directed functionalization of DNA and subsequent amine-specific chemoligations with various reporter groups. The demonstrated two-step sequence-specific labeling of natural DNA offers a facile way to query the methylation status of the target sites and envisions numerous applications in functional studies and medical diagnostics.

  DOI：

  10.1021/ja0691876

文献信息

• NEW S-ADENOSYL-L-METHIONINE ANALOGS WITH EXTENDED ACTIVATED GROUPS FOR TRANSFER BY METHYLTRANSFERASES
  申请人：RWTH Aachen

  公开号：EP1874790B1

  公开（公告）日：2010-08-18
• S-ADENOSYL-L-METHIONINE ANALOGS WITH EXTENDED ACTIVATED GROUPS FOR TRANSFER BY METHYLTRANSFERASES
  申请人：Weinhold Elmar

  公开号：US20090018101A1

  公开（公告）日：2009-01-15

  S-Adenosyl- L -methionine analogs of formula (I) wherein R comprises a carbon-carbon double bond, carbon-oxygen double bond, carbon-sulfur double bond, carbon-nitrogen double bond, a carbon-carbon triple bond, carbon-nitrogen triple bond or an aromatic carbocyclic or heterocyclic system in β-position to the sulfonium center, X— is an organic or inorganic anion carrying one or more negative charges, Z is —CR 1 R 2 —, —O—, —S— or —NR 3 — and R 1 , R 2 and R 3 are independently selected from H, D and C 1 -C 12 alkyl. Also disclosed are complexes of the compound with a methyltransferase, pharmaceutical compositions comprising the same, methods for modifying biomolecule using the compound, and methods for detecting sequences specific methylation of biomolecules using the compound.
• US8008007B2
  申请人：——

  公开号：US8008007B2

  公开（公告）日：2011-08-30
• Targeted Labeling of DNA by Methyltransferase-Directed Transfer of Activated Groups (mTAG)
  作者：Gražvydas Lukinavičius、Vidmantas Lapienė、Zdislav Staševskij、Christian Dalhoff、Elmar Weinhold、Saulius Klimašauskas

  DOI：10.1021/ja0691876

  日期：2007.3.1

  Methyltransferases catalyze highly specific transfers of methyl groups from the ubiquitous cofactor S-adenosyl-L-methionine (AdoMet) to various biopolymers like DNA, RNA, and proteins. Here we describe the first synthetic analogue of AdoMet with an activated side chain carrying a primary amino group that permits efficient methyltransferase-directed functionalization of DNA and subsequent amine-specific chemoligations with various reporter groups. The demonstrated two-step sequence-specific labeling of natural DNA offers a facile way to query the methylation status of the target sites and envisions numerous applications in functional studies and medical diagnostics.