H-D-Val-Pro-Sar-OBu^t | 5616-83-1

• 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: H-D-Val-Pro-Sar-OBu^t
• 英文别名: Glycine, N-methyl-N-(1-D-valyl-L-prolyl)-, 1,1-dimethylethyl ester；tert-butyl 2-[[(2S)-1-[(2R)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]-methylamino]acetate
• CAS: 5616-83-1
• 化学式: C₁₇H₃₁N₃O₄
• 分子量: 341.451
• InChiKey: KMGSXPFCIJQLQH-GXTWGEPZSA-N

物化性质

• 沸点：
  495.5±45.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-D-Val-Pro-Sar-OBu^t 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三氟甲磺酸 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 HONB 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 141.34h， 生成 更生霉素
  参考文献：
  名称：

  溶液和固态放线菌素相关肽内酯的构象和二聚化

  摘要：

  制备内酯 peptidiques 明显 a l'actinomycine et des actinomycinesrespondantes。Etude par RMN de 1 H des proprietes en solution de ces composes。结构结晶

  DOI：

  10.1021/ja00310a065
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-D-valylprolylsarcosine tert-butyl ester 在 palladium on activated charcoal 1,4-环己二烯 作用下， 以 乙醇 为溶剂， 生成 H-D-Val-Pro-Sar-OBu^t
  参考文献：
  名称：

  溶液和固态放线菌素相关肽内酯的构象和二聚化

  摘要：

  制备内酯 peptidiques 明显 a l'actinomycine et des actinomycinesrespondantes。Etude par RMN de 1 H des proprietes en solution de ces composes。结构结晶

  DOI：

  10.1021/ja00310a065

文献信息

• Highly Efficient Synthesis of Sterically Hindered Peptides Containing N-Methylated Amino Acid Residues using a Novel 1H-Benzimidazolium Salt
  作者：Peng Li、Jie Cheng Xu

  DOI：10.1016/s0040-4020(00)00963-7

  日期：2000.12

  Novel 1H-benzimidazolium type peptide coupling reagent, CMBI, was designed, synthesized, and shown to be efficient in the promotion of the formation of sterically hindered amide and ester bonds. Its high efficiency was proved by model reaction tests and the successful synthesis of various hindered oligopeptides and peptide segments containing N-methyl amino acid residues with fast reaction speeds, low

  设计，合成了新型1 H-苯并咪唑型肽偶联剂CMBI，证明其在促进空间位阻酰胺和酯键形成方面是有效的。通过模型反应试验和成功合成了各种受阻寡肽和含有N-甲基氨基酸残基的肽段，证明了其高效率，其反应速度快，外消旋化程度低且产率高。提出了由试剂介导的酰胺键形成机理。
• Toward the Design of an RNA:DNA Hybrid Binding Agent
  作者：Wenhua Chu、Shigehiro Kamitori、Miho Shinomiya、Robert G. Carlson、Fusao Takusagawa

  DOI：10.1021/ja00085a002

  日期：1994.3

  One characteristic function of the retroviruses, which is generally not found in normal eukaryotic cells, is production of a long RNA:DNA hybrid in the viral replication phase. If agents are designed which bind only to the RNA:DNA hybrid, but neither to DNA nor to RNA, such agents will be able to inhibit specifically the RNase H activity of retroviral reverse transcriptase, and therefore will suppress viral replication. Actinomycin D binds to double-stranded DNA, but not to RNA, because steric hindrance between the 2-amino group of the phenoxazinone ring and the 2'-hydroxyl group of RNA prevents intercalation of the antibiotic. However, if the C8-H in the phenoxazinone ring is replaced by an aromatic nitrogen N8, a strong hydrogen bond acceptor, this analog (N8-actinomycin D) might be able to bind intercalatively to an RNA:DNA hybrid by forming an additional hydrogen bond between N8 and the 2'-hydroxyl group of guanosine ribose. This hypothesis has been tested by a molecular mechanics calculation using a model structure of the complex between N8-actinomycin D and a small RNA:DNA hybrid, r(GC):d(GC). The results of the molecular mechanics calculation suggest that N8-actinomycin D can intercalatively bind to the RNA: DNA hybrid by making an additional intracomplex hydrogen bond. This hydrogen bonding capability of N8 has been confirmed in the crystal structure of the chromophore of N8-actinomycin D. Thus, N8-actinomycin D has been synthesized by coupling the pyridine and benzene fragments obtained independently. A binding study indicates that both actinomycin D and N8-actinomycin D bind intercalatively not only to DNA:DNA double strands but also to RNA:DNA hybrids. Although the overall binding capacity of N8-actinomycin D is reduced substantially in comparison with that of actinomycin D itself, N8-actinomycin D tends to bind relatively more favorably than actinomycin D to the RNA:DNA hybrids. Thus, this initial attempt at designing an RNA:DNA hybrid binding agent appears to be successful. However, it is necessary to modify the agent further to increase its RNA:DNA hybrid binding character and to decrease the DNA:DNA binding character, in order to make a useful RNA:DNA hybrid binding agent.
• MAUGER, ANTHONY B.;STUART, OSWALD A., INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 4, 481-488
  作者：MAUGER, ANTHONY B.、STUART, OSWALD A.

  DOI：——

  日期：——