(benzyloxycarbonyl)sarcosine tert-butyl ester | 101644-79-5

• 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: (benzyloxycarbonyl)sarcosine tert-butyl ester
• 英文别名: Tert-butyl 2-[methyl(phenylmethoxycarbonyl)amino]acetate
• CAS: 101644-79-5
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: VVOJZJXPFURAIA-UHFFFAOYSA-N

物化性质

• 沸点：
  371.9±31.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (benzyloxycarbonyl)sarcosine tert-butyl ester 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -10.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 N-(benzyloxycarbonyl)-D-valylprolylsarcosine tert-butyl ester
  参考文献：
  名称：

  Toward the Design of an RNA:DNA Hybrid Binding Agent

  摘要：

  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.

  DOI：

  10.1021/ja00085a002
• 作为产物：
  描述：

  氯甲酸苄酯 在 吡啶 、 silver(l) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 (benzyloxycarbonyl)sarcosine tert-butyl ester
  参考文献：
  名称：

  脂质霉素 - 对核糖基二氮杂环酮部分的合成研究

  摘要：

  根据灵活的不对称合成策略，描述了对映体纯 2-ribosyl-1,4-diazepan-3-one 核心 liposidomycins 的合成，这是一类复杂的脂质核苷抗生素。它涉及两个结构单元，一个是从 L-抗坏血酸中容易获得的对映体纯 α-叠氮基-β,γ-环氧丁醇，另一个是从 D-核糖中获得的 α-核糖基氨基酸。随后通过氨基酸对环氧化物的区域特异性亲核打开进行环化，然后进行肽偶联，得到目标核糖基二氮杂环酮。

  DOI：

  10.1002/1099-0690(200108)2001:16<3089::aid-ejoc3089>3.0.co;2-l

文献信息

• Trimethyl-Substituted Carbamate as a Versatile Self-Immolative Linker for Fluorescence Detection of Enzyme Reactions
  作者：Noriaki Nakamura、Shohei Uchinomiya、Kazuya Inoue、Akio Ojida

  DOI：10.3390/molecules25092153

  日期：——

  (i.e., trimethyl) carbamate as a new class of self-immolative linker for the fluorescence detection of enzyme reactions. The trimethyl carbamate was shown to spontaneously undergo intramolecular cyclization upon formation of a carboxylate group, to liberate a fluorophore with the second time rapid reaction kinetics. Interestingly, the auto-cleavage reaction of trimethyl carbamate was also induced by

  自焚接头是分子探针的有用构建块，在酶活性分析、刺激响应材料科学和药物递送领域具有广泛的应用。这份手稿将 N-甲基二甲基甲基（即三甲基）氨基甲酸酯作为一类用于酶反应荧光检测的新型自焚接头。氨基甲酸三甲酯显示出在形成羧酸酯基团后自发地进行分子内环化，以第二次快速反应动力学释放荧光团。有趣的是，氨基甲酸三甲酯的自动裂解反应也是由羟基和氨基的形成引起的。含氨基甲酸三甲酯的荧光探针可用于酯酶、酮还原酶、
• SYNTHESIS OF POSSIBLE ACTINOMYCIN D PRECURSORS
  作者：John P. Marsh Jr.、Leon Goodman

  DOI：10.1139/v66-114

  日期：1966.4.1

  The preparation of a number of polypeptides whose sequences are found in the actinomycin D molecule is described. The 4-methyl-3-hydroxyanthranoyl derivatives cf these peptides were also prepared as possible substrates for an enzyme that forms the phenoxazinone system of the antibiotic.

  描述了其序列在放线菌素 D 分子中发现的许多多肽的制备。这些肽的 4-甲基-3-羟基蒽酰基衍生物也被制备为可能的酶底物，酶形成抗生素的吩恶嗪酮系统。
• Hydroxy substituted ureido amino and imino acids
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04604402A1

  公开（公告）日：1986-08-05

  Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.

  公式为##STR1##的化合物已被披露。这些化合物由于其抑制血管紧张素转化酶的活性而被用作降压剂，并根据X的定义，也可能由于其脑啡肽酶抑制活性而被用作止痛剂。
• 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。
• A short synthesis of enantiomerically pure (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid, the unusual C9 amino acid found in the immunosuppressive peptide cyclosporine
  作者：Johannes D. Aebi、Madhup K. Dhaon、Daniel H. Rich

  DOI：10.1021/jo00389a041

  日期：1987.6