4-[(tert-butoxycarbonylamino)butanamido]but-2-yn-1-ol | 912477-39-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[(tert-butoxycarbonylamino)butanamido]but-2-yn-1-ol
• 英文别名: 4-[(tert.-B utoxycarbonylamino)butanamido]but-2-yn-1-ol；tert-butyl N-[4-(4-hydroxybut-2-ynylamino)-4-oxobutyl]carbamate
• CAS: 912477-39-5
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: JFSDFFJIFLEWCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(tert-butoxycarbonylamino)butanamido]but-2-yn-1-ol 在 sodium hydroxide 、 甲酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  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 、 4-aminobut-2-yn-1-ol hydrochloride 在 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以52%的产率得到4-[(tert-butoxycarbonylamino)butanamido]but-2-yn-1-ol
  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

• S-adenosyl-L-methionine analogs with extended activated groups for transfer by methyltransferases
  申请人：RWTH Aachen

  公开号：US08008007B2

  公开（公告）日：2011-08-30

  S-Adenosyl-L-methionine analogs of formula (I): are disclosed wherein R comprises a carbon-carbon 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, Xcircle around (−)} is an organic or inorganic anion carrying one or more negative charges, Z is —CR1R2—, —O—, —S— or —NR3— and R1, R2 and R3 are independently selected from H, D and C1—C alkyl; as well as complexes with a methyltransferase, pharmaceutical compositions, methods for modifying a biomolecule, and methods for detecting sequences specific methylation of biomolecules.

  公开了化学式（I）的S-腺苷基-L-甲硫氨酸类似物，其中R包括碳-碳双键，碳-硫双键，碳-氮双键，碳-碳三键，碳-氮三键或位于磺酸中心的β位的芳香族碳环或杂环系统，X circle around (-)}是携带一个或多个负电荷的有机或无机阴离子，Z是-CR1R2-，-O-，-S-或-NR3-，其中R1，R2和R3独立选择自H，D和C1-C烷基；以及与甲基转移酶的复合物，制备修饰生物分子的药物组合物，检测特定甲基化生物分子序列的方法。
• 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.