t-BOC-L-Alanine 2,2,2-Trichloroethyl Ester | 86555-51-3

• 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: t-BOC-L-Alanine 2,2,2-Trichloroethyl Ester
• 英文别名: N-[(1,1-Dimethylethoxy)carbonyl]-L-alanine 2,2,2-trichloroethyl ester；2,2,2-trichloroethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 86555-51-3
• 化学式: C₁₀H₁₆Cl₃NO₄
• 分子量: 320.6
• InChiKey: APBCFGNBGOTMTH-LURJTMIESA-N

物化性质

• 熔点：
  67 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  420.4±45.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-BOC-L-Alanine 2,2,2-Trichloroethyl Ester 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 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 16.0h， 生成 2,2,2-trichloroethyl N-(N-(D-alanyl)-N-methyl-L-phenylalanyl)-N-methylglycyl-L-isoleucyl-L-alaninate hydrochloride
  参考文献：
  名称：

  The total synthesis and structure–activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

  摘要：

  We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-L-Ala, 24-D-MePhe, 37-L-Ile, 43-D-Ala, 15-D-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure activity relationships of kulokekahilide-2 and its analogs indicate the importance of an L-amino acid at position 21. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.094
• 作为产物：
  描述：

  2,2,2-三氯乙醇 、 N-叔丁氧羰基-L-丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 t-BOC-L-Alanine 2,2,2-Trichloroethyl Ester
  参考文献：
  名称：

  高效合成地二恶英A和jasbamide，海洋海绵来源的细胞毒性和抗真菌环状二肽

  摘要：

  通过使用Evans不对称烷基化，Mitsunobu酯化和DPPA大内酰胺化作为关键步骤，有效地合成了Geodiamolide A（1a）和jaspamide（2）。

  DOI：

  10.1016/s0040-4039(00)75846-1

文献信息

• Synthesis of a close analog of the repeating unit of the antifreeze glycoproteins of polar fish
  作者：Abul Kashem M. Anisuzzaman、Laurens Anderson、Juan L. Navia

  DOI：10.1016/0008-6215(88)85096-1

  日期：1988.3

  Alternatively, the 1-propenyl intermediate was obtained directly by using 1-propenyl 2,4,6-tri-O-benzyl-alpha-D-galactopyranoside as the acceptor in the initial coupling reaction. An efficient 3-step synthesis of 10 was accomplished by the dibutyltin oxide-assisted, selective crotylation of allyl alpha-D-galactopyranoside at O-3, followed by benzylation and treatment of the product with potassium tert-butoxide

  被保护的糖肽N-（苄氧羰基）-L-丙氨酰基-[O-（2,3,4,6-四-O-苯甲酰基-β-D-吡喃半乳糖基）-（1-3）-O-（通过偶合2,4,6-三-O-苄基-α-D-吡喃半乳糖（1 ---- 3）]-L-苏氨酰基-L-丙氨酸2,2,2-三氯乙基酯各自的二糖和三肽嵌段。通过将四-O-苯甲酰基-α-D-半乳糖吡喃糖基溴化物偶联到烯丙基2,4,6-三-O-苄基-α-D-吡喃半乳糖苷并将产物转化为O-（2,3，通过1-丙烯基糖苷的4,6-四-O-苯甲酰基-β-D-吡喃半乳糖基）-（1 ---- 3）-2,4,6-三-O-苄基-α-D-吡喃半乳糖基氯和游离的（1-OH）糖。或者，在初始偶联反应中，通过使用1-丙烯基2,4,6-三-O-苄基-α-D-吡喃半乳糖苷直接作为受体，获得1-丙烯基中间体。通过在O-3处烯丙基α-D-吡喃半乳糖苷的二丁基氧化锡辅助的选择性丁酰化，然后进行苄基化和用叔丁醇钾处
• The Conformation of<b><i>de</i></b><b><i>Novo</i></b>Designed Amphiphilic Peptides with Six or Nine<b>L</b>-2-(2,2,2-Trifluoroethyl)glycines as the Hydrophobic Amino Acid
  作者：Toru Arai、Takashi Imachi、Tamaki Kato、Norikazu Nishino

  DOI：10.1246/bcsj.73.439

  日期：2000.2

  L-2-(2,2,2-trifluoroethyl)glycines took a helical conformation in H2O containing a > 20% volume of 2,2,2-trifluoroethanol. These facts suggested the hydrophobic nature of the L-trifluoroethylglycines. The peptide with six L-2-(2,2,2-trifluoroethyl)glycines took a helical structure in methanol, however it slowly changed into the β-structure within 24 h. Interestingly, the peptide with nine L-2-(2,2,2-tri

  合成了具有 6 个和 9 个 L-2-(2,2,2-三氟乙基) 甘氨酸作为疏水性氨基酸和赖氨酸和谷氨酸作为亲水性氨基酸的两亲性 21 肽。CD 光谱显示这些带有 L-2-(2,2,2-三氟乙基) 甘氨酸的肽在 H2O 中呈随机构象。相反，具有亮氨酸作为疏水性氨基酸的类似两亲性 21 肽在 中呈螺旋构象。具有 L-2-(2,2,2-三氟乙基) 甘氨酸的肽在含有 > 20% 体积的 2,2,2-三氟乙醇的 中呈现螺旋构象。这些事实表明L-三氟乙基甘氨酸的疏水性。含有六个 L-2-(2,2,2-三氟乙基)甘氨酸的肽在甲醇中呈螺旋结构，但在 24 小时内缓慢转变为 β 结构。有趣的是，肽含有 9 个 L-2-(2,2, 2-三氟乙基）甘氨酸在相同条件下形成稳定的螺旋。具有九个 L-2-(2,2,2-三氟乙基)甘氨酸的肽优选螺旋结构，可能...
• Peptide-type substrates useful in the quantitative determination of
  申请人：Mallinckrodt, Inc.

  公开号：US04406832A1

  公开（公告）日：1983-09-27

  Disclosed are chromogenic or fluorogenic peptide-type compounds adapted for use in determining endotoxin in a sample by a Limulus amebocyte lysate-type assay. The compounds have the general formula: R.sub.1 -A.sub.1 -A.sub.2 -A.sub.3 -A.sub.4 -B-R.sub.2 wherein R.sub.1 represents hydrogen, a blocking aromatic hydrocarbon or acyl; A.sub.1 represents an L or D-amino acid selected from either Ileu, Val or Leu; A.sub.2 represents Glu or Asp; A.sub.3 represents Ala or Cyst; A.sub.4 represents Arg, B represents a linkage group selected from ester and amide linkage groups; and R.sub.2 represents a chromogenic or fluorogenic group which is covalently attached to the C-carboxyl terminal of arginine through the B linkage group and which yields a chromophoric or fluorescent marker compound of the formula R.sub.2 -B-H upon enzymatic hydrolysis from the remainder of the peptide-type compound by activated LAL pro-clot enzyme. Also disclosed are methods for the determination of endotoxin in a sample by contacting the sample with a pro-clotting enzyme from Limulus amebocyte lysate and one of the above chromogenic or fluorogenic peptide-type compounds.

  本发明涉及一种适用于利用Limulus amebocyte lysate型测定法测定样品中内毒素的色素或荧光肽类化合物。该化合物具有以下通式：R.sub.1 -A.sub.1 -A.sub.2 -A.sub.3 -A.sub.4 -B-R.sub.2，其中R.sub.1代表氢、阻断芳香烃或酰基；A.sub.1代表从Ileu、Val或Leu中选择的L或D-氨基酸；A.sub.2代表Glu或Asp；A.sub.3代表ALA或Cyst；A.sub.4代表Arg，B代表从酯和酰胺连接基中选择的连接基；R.sub.2代表与B连接基通过C-羧基末端与精氨酸共价连接的色素或荧光基团，并且在被激活的LAL前凝血酶酶解剩余的肽类化合物时生成化色或荧光标记化合物R.sub.2 -B-H。本发明还涉及一种通过将样品与来自Limulus amebocyte lysate的前凝血酶酶接触和上述的色素或荧光肽类化合物之一来测定样品中内毒素的方法。
• An Expeditious Synthesis of Geodiamolide A, an 18-Membered Cytotoxic Depsipeptide from Marine Sponges
  作者：Takayuki Shioiri、Takayuki Imaeda、Yasumasa Hamada

  DOI：10.3987/com-97-s41

  日期：——

  Geodiamolide A (1) has been efficiently synthesized from the polypropionate and tripeptide units using the Evans asymmetric alkylation, the Mitsunobu esterification, and the macrolactamization with diphenyl phosphorazidate (DPPA) as key steps. Efficient esterification between the complex polyketide and tripeptide units was also realized under high pressure conditions.
• KASHEM, ABUL;ANISUZZAMAN, M.;ANDERSON, LAURENS;NAVIA, JUAN L., CARBOHYDR. RES., 174,(1988) 265-278
  作者：KASHEM, ABUL、ANISUZZAMAN, M.、ANDERSON, LAURENS、NAVIA, JUAN L.

  DOI：——

  日期：——