N-[3-[[(1,1-二甲基乙氧基)羰基]氨基]丙基]-N-[(9H-芴-9-基甲氧基)羰基]-甘氨酸 | 143192-31-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-[3-[[(1,1-二甲基乙氧基)羰基]氨基]丙基]-N-[(9H-芴-9-基甲氧基)羰基]-甘氨酸
• 中文别名: FMOC--N-(3-BOC-氨基丙基)甘氨酸
• 英文名称: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-(5-((tert-butoxycarbonyl)amino)propyl)glycine
• 英文别名: Fmoc-N-(3-Boc-aminopropyl)-Gly-OH；2-[9H-fluoren-9-ylmethoxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]acetic acid
• CAS: 143192-31-8
• 化学式: C₂₅H₃₀N₂O₆
• 分子量: 454.523
• InChiKey: IMAPLGVUJDLQCK-UHFFFAOYSA-N

物化性质

• 沸点：
  649.3±48.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  硫代异氰酸苯酯 、 N-[3-[[(1,1-二甲基乙氧基)羰基]氨基]丙基]-N-[(9H-芴-9-基甲氧基)羰基]-甘氨酸 生成 1-(3-Amino-propyl)-3-phenyl-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  通过埃德曼降解法对类肽拟肽进行测序

  摘要：

  描述了通过测序直接鉴定树脂结合的类肽拟肽。用异硫氰酸苯酯处理拟肽的N-末端，然后从树脂上裂解N-末端拟肽残基作为其硫代乙内酰脲衍生物。为了推导类肽序列，将获得的巯基乙内酰脲的HPLC保留时间与独立制备的参考巯基乙内酰脲的HPLC保留时间进行了比较。

  DOI：

  10.1016/s0040-4039(98)00556-5
• 作为产物：
  描述：

  叔-丁基(3-(苯甲基氨基)丙基)氨基甲酯 在 palladium on activated charcoal 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 11.5h， 生成 N-[3-[[(1,1-二甲基乙氧基)羰基]氨基]丙基]-N-[(9H-芴-9-基甲氧基)羰基]-甘氨酸
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e

文献信息

• Peptide/Peptoid Hybrid Oligomers: The Influence of Hydrophobicity and Relative Side-Chain Length on Antibacterial Activity and Cell Selectivity
  作者：Nicki Frederiksen、Paul R. Hansen、Fredrik Björkling、Henrik Franzyk

  DOI：10.3390/molecules24244429

  日期：——

  relationships within a subclass of oligomers displaying variation of three structural features: (i) cationic side-chain length, (ii) hydrophobic side-chain length, and (iii) type of residue that is of a flexible peptoid nature. Increased side-chain length of cationic residues led to reduced hydrophobicity till the side chains became more extended than the aromatic/hydrophobic side chains, at which point

  先前对肽/拟肽杂交体的优化研究通常包括比较显示不同寡聚体长度和不同侧链的结构相关类似物。目前的工作涉及系统构建的一系列 16 个密切相关的 12 聚体低聚物，具有交替的阳离子/疏水设计，代表了广泛的疏水性和相对侧链长度的差异。目的是探索和合理化显示三个结构特征变化的低聚物亚类内的结构 - 活性关系：（i）阳离子侧链长度，（ii）疏水侧链长度，以及（iii）残基类型具有灵活的拟肽性质。阳离子残基侧链长度的增加导致疏水性降低，直到侧链变得比芳香族/疏水性侧链更长，此时疏水性略有增加。抗菌活性评估表明，具有最低疏水性的类似物对大肠杆菌的活性降低，而具有最短阳离子侧链的低聚物对铜绿假单胞菌最有效。因此，与铜绿假单胞菌的膜破坏相互作用似乎是由低聚物的疏水表面（由保护阳离子侧链的芳族基团组成）促进的。具有短阳离子侧链的肽模拟物表现出增加的溶血特性以及降低 HepG2（肝母细胞瘤 G2 细胞系）细胞活力。
• Synthesis and Biological Activity of NK-1 Selective, N-Backbone Cyclic Analogs of the C-Terminal Hexapeptide of Substance P
  作者：Gerardo Byk、David Halle、Irena Zeltser、Gal Bitan、Zvi Selinger、Chaim Gilon

  DOI：10.1021/jm960154i

  日期：1996.1.1

  backbone cyclization to linear substance P (SP) analogs is presented. We describe the synthesis, characterization, and biological activity of a series of backbone-to-amino-terminus cyclic analogs of the C-terminal hexapeptide of SP. These analogs were designed on the basis of NMR data and molecular modeling of the selective NK-1 analog WS-septide (Ac[Arg6,Pro9]SP6-11). A series of peptides with the

  介绍了骨架环化概念在线性物质P（SP）类似物中的应用。我们描述了SP的C端六肽的一系列骨架到氨基端的环状类似物的合成，表征和生物学活性。这些类似物是根据NMR数据和选择性NK-1类似物WS-肽（Ac [Arg6，Pro9] SP6-11）的分子模型设计的。一系列具有以下通式的肽：环[-CH2）m-NH-CO-（ ）n-CO-Arg-Phe-Phe-N-]- -CO-Leu-Met-NH2（n = 2 ，3、6和m = 2、3、4）是通过固相方法合成的，使用Fmoc化学作为主链，Boc化学用于构建单元[Na-（ω-氨基烷基）Gly]侧链。从ω-氨基烷基链上除去Boc保护基后，对树脂进行环化。比较了环状和环状前类似物。它们通过HPLC纯化，并通过质谱和NMR进行表征。发现对NK-1神经激肽受体的生物活性和选择性取决于环化和环的大小：最具活性和选择性的类似物具有20个原子的环。与WS-肽
• COMPOUNDS USEFUL IN PREPARING HYBRID IMMUNOGLOBULIN CONTAINING NON-PEPTIDYL LINKAGE
  申请人：Capon, Daniel J.

  公开号：EP3701971A1

  公开（公告）日：2020-09-02

  The present invention provides intermediate compounds containing a triazine or trans-cyclooctene group, useful in the preparation of compounds having the structure:         A-B-----Z wherein A is a biologically active structure of the compound; wherein Z is a protein component of the compound, which protein component comprises one or more polypeptides, wherein at least one of the one or more polypeptides comprises consecutive amino acids which (i) are identical to a stretch of consecutive amino acids present in a chain of an Fc domain of an antibody; (ii) bind to an Fc receptor; and (iii) have at their N-terminus a sequence selected from the group consisting of a cysteine or selenocysteine; wherein the dashed line between B and Z represents a peptidyl linkage; and wherein the solid line between A and B represents a nonpeptidyl linkage.

  本发明提供了含有三嗪或反式环辛烯基团的中间体化合物，可用于制备具有以下结构的化合物： A-B-----Z 其中，A 是化合物的生物活性结构；Z 是化合物的蛋白质成分，该蛋白质成分包括一个或多个多肽，其中一个或多个多肽中至少有一个多肽包括连续氨基酸，这些连续氨基酸(i) 与抗体 Fc 结构域链中存在的一段连续氨基酸相同；(ii)与 Fc 受体结合；以及(iii)在其 N 端具有选自半胱氨酸或硒半胱氨酸组成的组的序列；其中 B 和 Z 之间的虚线代表肽基连接；而 A 和 B 之间的实线代表非肽基连接。
• Hybrid immunoglobulin containing non-peptidyl linkage
  申请人：Biomolecular Holdings LLC

  公开号：US11066459B2

  公开（公告）日：2021-07-20

  The present invention provides a compound having the structure: A-B - - - Z wherein A is a biologically active structure of the compound; wherein Z is a protein component of the compound, which protein component comprises one or more polypeptides, wherein at least one of the one or more polypeptides comprises consecutive amino acids which (i) are identical to a stretch of consecutive amino acids present in a chain of an Fc domain of an antibody; (ii) bind to an Fc receptor; and (iii) have at their N-terminus a sequence selected from the group consisting of a cysteine or selenocysteine; wherein the dashed line between B and Z represents a peptidyl linkage; and wherein the solid line between A and B represents a nonpeptidyl linkage, as well as intermediates dimers thereof, and processes of producing the compounds of the invention.

  本发明提供了一种具有以下结构的化合物： A-B - - Z 其中 A 是该化合物的生物活性结构；其中 Z 是该化合物的蛋白质组分，该蛋白质组分包括一个或多个多肽，其中一个或多个多肽中的至少一个多肽包括连续氨基酸，这些连续氨基酸(i) 与抗体的 Fc 结构域链中存在的一段连续氨基酸相同；(ii)与 Fc 受体结合；(iii)在其 N 端具有选自由半胱氨酸或硒半胱氨酸组成的组的序列；其中 B 和 Z 之间的虚线表示肽基连接；A 和 B 之间的实线表示非肽基连接，以及其中间体二聚体，以及生产本发明化合物的工艺。
• Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units
  作者：Gerardo Byk、Chaim Gilon

  DOI：10.1021/jo00047a022

  日期：1992.10

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.