Boc-Aib-NCA

• 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: Boc-Aib-NCA
• 英文别名: Tert-butyl 4,4-dimethyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate
• 化学式: C₁₀H₁₅NO₅
• 分子量: 229.233
• InChiKey: PCEGYIBEZAVPRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Aib-NCA 在 N-甲基吗啉 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 102.0h， 生成
  参考文献：
  名称：

  New crown-carrier Cα,α-disubstituted glycines derived from α-methyl-(l)-DOPA

  摘要：

  The side-chain catechol function of alpha-methyl-(L)-DOPA was utilized for the synthesis of a new series of crown-carrier C-alpha,C-alpha-disubstituted glycines. During N-protection of alpha-methyl-(L)-DOPA methyl ester (H-Mdp-OMe) with Boc anhydride, the formation of N,O-di-Boc derivatives was observed. Selective aminolysis of the catechol tert-butyl carbonate group was achieved using pyrrolidine as nucleophile. Treatment of the resulting Boc-Mdp-OMe by Cs2CO3 in MeOH, followed by bis-O-alkylation with cyclization using various polyethyleneglycol ditosylates or catechol-derived bis-polyethyleneglycol ditosylates in DMF at 60degreesC, led to the derivatives Boc-[15-C-5]-Mdp-OMe, Boc-[18-C-6]-Mdp-OMe, Boc-[benzo-18-C-6]-Mdp-OMe, Boc-[benzo-24-C-8]-Mdp-OMe and then after saponification, to the corresponding N-alpha-protected amino acids. The tripeptides Fmoc-Ala-[18-C-6]-Mdp-Ala-OMe and Boc-Aib-[18-C-6]-Mdp-Ala-OMe were prepared in solution by using Ala and Aib UNCAs for coupling at the N terminus of the [18-C-6]-Mdp residue and the EDC/HOAt method for coupling Ala at its C terminus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00566-5

文献信息

• Acylation of Sugar Hydroxyl Groups with<i>N</i>-BOC Amino Acid<i>N</i>-Carboxyanhydrides (Boc-NCAs). Synthesis of Amino Acid-Saccharide Conjugates
  作者：Daniel Cabaret、Michel Wakselman、Aboucabar Kaba、Lulla Ilunga、Charles Chany

  DOI：10.1080/00397919808004842

  日期：1998.7

  Abstract Boc-NCAs cleanly react with a series of free or protected sugars to give mono-or poly-amino acid conjugates in good yields. Trifluoroacetic acid in methylene chloride only cleaves the N-Boc protecting group. Treatment with aqueous trifluoroacetic acid removes the remaining isopropylidene protecting groups and leads to free glycoconjugates.

  摘要 Boc-NCA 与一系列游离或受保护的糖完全反应，以良好的产率得到单或多氨基酸缀合物。二氯甲烷中的三氟乙酸仅裂解 N-Boc 保护基团。用三氟乙酸水溶液处理除去剩余的异亚丙基保护基团并产生游离的糖缀合物。
• Synthesis of protected derivatives and short peptides of antAib, a novel Cα-tetrasubstituted α-amino acid of the Ac5c type possessing a fused anthracene fluorophore
  作者：Jean-François Lohier、Karen Wright、Cristina Peggion、Fernando Formaggio、Claudio Toniolo、Michel Wakselman、Jean-Paul Mazaleyrat

  DOI：10.1016/j.tet.2006.04.055

  日期：2006.6

  The Nα-Boc and Nα-Fmoc protected derivatives of 2-amino-2,3-dihydro-1H-cyclopenta[b]anthracene-2-carboxylic acid (antAib), a novel fluorescent, achiral, α-amino acid, rigid analogue of the known 9-antAla and 2-antAla residues, and belonging to the class of Ciα→Ciα cyclized, Cα,α-disubstituted glycines (strong β-turn and helix inducers in peptides), were synthesized in seven steps from 1,2,4-trimethylbenzene

  所述Ñ α -Boc和Ñ α -Fmoc保护的2-氨基-2,3-二氢-1衍生物ħ环戊二烯并[ b ]蒽-2-羧酸（antAib），一种新型的荧光，非手性，α氨基酸中，已知的9-antAla和2- antAla残基的刚性类似物，和属于类的ç我α →交通ç我α环化，ç α，α从1,2,4-三甲基苯分七个步骤合成了α-二取代的甘氨酸（肽中的强β-转角和螺旋诱导剂）。还描述了Boc–antAib–OEt和Boc–antAib–OH的紫外线吸收和荧光特性。短肽Boc–antAib–1–Ala–OMe，Fmoc–1–Ala–antAib–1–Ala–OMe以及Boc–Aib–antAib–1–Ala–OMe和副产物的溶液合成2提出了5-二氧杂哌嗪环-[antAib-1-Ala]作为antAib残基在C-和N-末端的偶联能力的例子。
• 9-Amino-4,5-diazafluorene-9-carboxylic Acid (Daf), a New Cα,α-Disubstituted Glycine Containing a Spatially Constrained Bipyridine-Like Ligand for Transition Metals − Synthesis and Evaluation of Peptide-Coupling Conditions at itsC- andN-Termini
  作者：Jean-Paul Mazaleyrat、Karen Wright、Michel Wakselman、Fernando Formaggio、Marco Crisma、Claudio Toniolo

  DOI：10.1002/1099-0690(200105)2001:10<1821::aid-ejoc1821>3.0.co;2-9

  日期：2001.5

  method. Coupling of Boc-Ala-OH at the N-terminus of Daf could also be performed by the mixed anhydride method. However, coupling of the crowded Aib residue required the use of Boc-Aib-NCA. Daf, a new Cα,α-disubstituted glycine, is the first α-amino acid containing a rigid bipyridine ligand in a totally controlled spatial disposition relative to the Cα atom.

  N-苄基-4,5-二氮杂芴-9-亚甲基胺的阴离子与氯甲酸甲酯或苄酯酰化，然后进行酸性水解，生成 9-氨基-4,5-二氮杂芴-9-甲酸甲酯（H- Daf-OMe) 和苄酯 (H-Daf-OBzl)。在 60 °C 下用 Boc2O 进行 Nα-保护得到 Boc-Daf-OMe 和 Boc-Daf-OBzl，其皂化或氢解导致完全脱羧。然而，酯官能团的肼解提供了 Boc-Daf-NHNH2，它通过酰叠氮化物方法与 H-Ala-OMe 有效偶联。Boc-Ala-OH 在 Daf 的 N 端偶联也可以通过混合酸酐方法进行。然而，拥挤的 Aib 残基的偶联需要使用 Boc-Aib-NCA。Daf，一种新的 Cα,α-二取代甘氨酸，
• Synthesis of enantiopure, axially chiral, Cα-tetrasubstituted α-amino acids with binaphthyl-based crowned side chains and 3D-structural analysis of their peptides
  作者：Karen Wright、Jean-François Lohier、Michel Wakselman、Jean-Paul Mazaleyrat、Fernando Formaggio、Cristina Peggion、Marta De Zotti、Claudio Toniolo

  DOI：10.1016/j.tet.2008.01.019

  日期：2008.3

  acid (Bip), were performed by bis-alkylation with cyclization of racemic (R+S)-Boc-[HO]2-Bip-OMe, possessing two phenolic OH groups at the 6,6′-positions of the biphenyl frame of Bip, using (+)-(R)- and (−)-(S)-Binol[(OCH2CH2)2OTs]2 (2,2′-bis[5-tosyloxy-3-oxa-1-pentyloxy]-1,1′-binaphthyl), respectively, as the alkylating agent followed by chromatographic separation. Two series of terminally protected

  的末端的保护，冠，所述合成Ç α -tetrasubstitutedα氨基与仅轴向手性，所述两种非对映的Boc-（酸小号）-Bip [（[R）-BINOL-22-C-6] -OMe和的Boc- （R）-Bip [（R）-Binol-22-C-6] -OMe和它们各自的对映异构体Boc-（R）-Bip [（S）-Binol-22-C-6] -OMe和Boc- （S）-Bip [（S）-Binol-22-C-6] -OMe，均衍生自2'，1'：1,2; 通过双烷基化和外消旋（R + S）-Boc- [HO]的环化反应，进行1''，2''：3,4-dibenzcyclohepta-1,3-diene-6-amino-6-羧酸（Bip）] 2-Bip-OMe，使用（+）-（R）-和（-）-（S）-Binol [（OCH 2 CH 2）2 OTs] 2（2,2'-双[5-甲苯磺酰氧基-3-氧杂-1-戊氧基]
• Synthesis, Ion Complexation Study, and 3D-Structural Analysis of Peptides Based on Crown-Carrier,Cα-Methyl-L-DOPA Amino Acids
  作者：Karen Wright、Rachid Anddad、Jean-François Lohier、Vincent Steinmetz、Michel Wakselman、Jean-Paul Mazaleyrat、Fernando Formaggio、Cristina Peggion、Marta De Zotti、Timothy A. Keiderling、Rong Huang、Claudio Toniolo

  DOI：10.1002/ejoc.200700917

  日期：2008.3

  terminally protected model peptides to the hexamer level, based on four novel, crown-ether containing Cα-methyl-L-DOPA (L-Mdp) amino acid residues, namely L-Mdp[15-C-5], L-Mdp[18-C-6], L-Mdp[benzo-24-C-8] and L-Mdp[(S)-Binol-20-C-6], combined with either L-Ala or L-Ala/Aib or Gly/Aib, were synthesized by solution methods. An ESI-MS analysis of their alkali metal cation complexation ability was carried out

  选定系列的六聚体水平的末端保护模型肽，基于四个新的、含 Cα-甲基-L-多巴 (L-Mdp) 氨基酸残基的冠醚，即 L-Mdp[15-C-5]、L -Mdp[18-C-6]、L-Mdp[benzo-24-C-8] 和 L-Mdp[(S)-Binol-20-C-6]，与 L-Ala 或 L-Ala 结合/Aib 或 Gly/Aib，通过溶液法合成。对其碱金属阳离子络合能力进行了 ESI-MS 分析。它们的 FTIR 吸收、1H NMR、ECD 和 VCD 光谱特性表明所有这些冠状氨基酸都是（左旋）β-转角和 310-螺旋结构的强诱导剂。（© Wiley-VCH Verlag GmbH & Co. KGaA , 69451 德国魏因海姆, 2008)