Cbz-L-Ala-Aib-OMe | 112142-82-2

• 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: Cbz-L-Ala-Aib-OMe
• 英文别名: methyl 2-methyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 112142-82-2
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: YPVMBEKPUHGPEB-NSHDSACASA-N

物化性质

• 熔点：
  118-120 °C(Solv: ethanol (64-17-5))
• 沸点：
  501.0±40.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cbz-L-Ala-Aib-OMe 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Efficient synthesis of alamethicin f-30 using a chloro imidazolidium coupling reagent, CIP

  摘要：

  Alamethicin F-30 has been synthesized in solution using a CIP-additive as a coupling agent and TFA as a final deprotecting reagent. All couplings including those between sterically hindered alpha,alpha-dimethyl amino acid were successfully achieved by a 60 min reaction.

  DOI：

  10.1016/0040-4039(95)02023-i
• 作为产物：
  描述：

  N-benzyloxycarbonyl-L-alanyl-N¹,N¹,2-trimethylalanin-amid 在 盐酸 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.67h， 生成 Cbz-L-Ala-Aib-OMe
  参考文献：
  名称：

  拟南芥肽肽α，α-二取代α-氨基

  摘要：

  含α，α-二取代α-氨基酸的肽的选择性酰胺裂解

  DOI：

  10.1002/hlca.19870700213

文献信息

• Practical Peptide Synthesis Mediated by a Recyclable Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine
  作者：Chi Zhang、Shan-Shan Liu、Bo Sun、Jun Tian

  DOI：10.1021/acs.orglett.5b02045

  日期：2015.8.21

  1,4-dione (p-BTFP-iodosodilactone, 1a) was synthesized and demonstrated to be an efficient hypervalent iodine(III) reagent for the synthesis of dipeptides from various standard amino acids, including sterically hindered amino acids, in good to high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine. In addition, the combined system of 1a/(4-MeOC6H4)3P was used to synthesize the

  6-（3,5-二（三氟甲基）苯基）-1 ħ，4 ħ -2aλ 3 -ioda -2,3- dioxacyclopenta [喜]茚-1,4-二酮（p -BTFP-iodosodilactone，1A）中的溶液在三（4-甲氧基苯基）膦的存在下，在30分钟内以高至高收率合成并证明是一种有效的高价碘（III）试剂，用于从各种标准氨基酸（包括位阻氨基酸）合成二肽。另外，使用1a /（4-MeOC 6 H 4）3 P的组合系统以保护形式合成五肽亮氨酸-脑啡肽。值得注意的是1a 反应后可以很容易地再生。
• Conformationally controlled, thymine-based α-nucleopeptides
  作者：Piero Geotti-Bianchini、Marco Crisma、Cristina Peggion、Alberto Bianco、Fernando Formaggio

  DOI：10.1039/b822789f

  日期：——

  Rigid peptide backbones and backbone-to-side chain H-bonds permit the design of α-nucleopeptides with known 3D-structure; thymine–thymine base pairing is also observed.

  刚性肽主链和主链与侧链之间的氢键使得能够设计具有已知三维结构的α-核肽；还观察到胸腺嘧啶–胸腺嘧啶的碱基配对。
• Oxidation-Induced Acyl Group Transfer from Hydroquinone Esters to Nucleophiles
  作者：Gerald Reischl、Medhat El-Mobayed、Rudolf Beißwenger、Klaus Regier、Cäcilia Maichle-Mössmer、Anton Rieker

  DOI：10.1515/znb-1998-0717

  日期：1998.7.1

  Bivalent oxidation of 3,5-di-tert-butyl-hydroquinone monoesters leads to phenoxenium ions, which can transfer an acyl group to nucleophiles. Based on this principle, dipeptides, glyco-amino acids and N-sulfonyl-amino acids were synthesized from hydroquinone esters of amino acids and p-toluenesulfonic acid. For this reaction, direct anodic and indirect mediated oxidation, as well as chemical oxidation with NBS or trisarylammoniumyl salts, was used. The mechanism of the acyl transfer is discussed in terms of a direct and/or a mediated process. A spirocyclic key intermediate was isolated and its molecular structure determined by X-ray crystallography.

  3,5-二叔丁基对羟基苯醌单酯的双价氧化会生成苯氧离子，可以将酰基转移给亲核试剂。基于这一原理，从氨基酸和对甲苯磺酸的苯醌酯合成了二肽、糖氨基酸和N-磺酰氨基酸。在这个反应中，使用了直接阳极和间接介导氧化，以及与NBS或三芳基铵盐的化学氧化。酰基转移的机理讨论了直接和/或介导过程。一个螺环键中间体被分离出来，并通过X射线晶体学确定了其分子结构。
• Fungal Metabolites. XVII. Synthesis and NMR Study of Ion Channel-Forming Peptides, Trichosporin B-VIa and Its Derivative.
  作者：Yasuo NAGAOKA、Akira IIDA、Teturo FUJITA

  DOI：10.1248/cpb.42.1258

  日期：——

  A membrane-modifying peptide antibiotic, trichosporin B-VIa, having catecholamine secretion-inducing activity on bovine adrenal chromaffin cells has been synthesized. Aib14-Trichosporin B-VIa, in which Pro14 was replaced by Aib, has also been synthesized to modify the secondary structure of trichosporin B-VIa. Sequience-specific 1H-NMR assignments of both peptides in methanol were achieved by using two-dimensional NMR techniques.

  我们合成了一种膜修饰肽抗生素--三碳卟啉 B-VIa，它对牛肾上腺绒毛细胞具有儿茶酚胺分泌诱导活性。此外，还合成了 Aib14-Trichosporin B-VIa，其中的 Pro14 被 Aib 取代，从而改变了三叶鞘磷脂 B-VIa 的二级结构。利用二维核磁共振技术实现了这两种肽在甲醇中的序列特异性 1H-NMR 分配。
• Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary
  作者：Beata Kolesinska、Zbigniew J. Kaminski

  DOI：10.1021/ol802691x

  日期：2009.2.5

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.