BOC-ALA-HOBt | 66024-53-1

• 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-ALA-HOBt
• 英文别名: BOC-Ala-POBT；Boc-Ala-OBt；benzotriazol-1-yl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 66024-53-1
• 化学式: C₁₄H₁₈N₄O₄
• 分子量: 306.321
• InChiKey: SXXHEXXGVWAQHC-VIFPVBQESA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BOC-ALA-HOBt 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.0h， 生成 Boc-Ala-Arg(Tos)-Pro-Ala-Lys(Z)-OH
  参考文献：
  名称：

  Zhao, Ming; Peng, Shiqi, Advanced Synthesis and Catalysis, 1999, vol. 341, # 7, p. 668 - 676

  摘要：

  DOI：
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 2.0h， 生成 BOC-ALA-HOBt
  参考文献：
  名称：

  Meldal, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 242 - 249

  摘要：

  DOI：

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• ¹⁸F-Trifluoromethylation of Unmodified Peptides with 5-¹⁸F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate
  作者：Stefan Verhoog、Choon Wee Kee、Yanlan Wang、Tanatorn Khotavivattana、Thomas C. Wilson、Veerle Kersemans、Sean Smart、Matthew Tredwell、Benjamin G. Davis、Véronique Gouverneur

  DOI：10.1021/jacs.7b10227

  日期：2018.2.7

  18F-labeling of 5-(trifluoromethyl)-dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, followed by oxidative cyclization with Oxone and trifluoromethanesulfonic anhydride. This new 18F-reagent allows for the direct chemoselective 18F-labeling of unmodified peptides at the thiol cysteine

  5-(三氟甲基)-二苯并噻吩三氟甲磺酸盐的 18F 标记，通常称为 Umemoto 试剂，已通过卤素交换 18F-氟化与 18F-氟化物，然后与 Oxone 和三氟甲磺酸酐氧化环化来完成。这种新的 18F 试剂允许在硫醇半胱氨酸残基处对未修饰的肽进行直接化学选择性 18F 标记。
• Synthesis of the octadecapeptide corresponding to positions 32 to 49 of the revised amino acid sequence of thymopoietin II and its effect on low E-rosette forming cells of an aged patient with chronic renal failure.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.30.3271

  日期：——

  The octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH, corresponding to positions 32 to 49 of the revised amino acid sequence of bovine thymopoietin II was synthesized by the azide condensation of three fragments, (32-36), (37-41) and (42-49), followed by deprotection with hydrogen fluoride in the presence of anisole-thioanisole-o-cresol. The in vitro addition of the synthetic thymopoietin II (32-49) significantly restored the low E-rosette forming capacity of cells from an aged patient with chronic renal failure to normal levels. The in vitro effect of [Gln38, Thr43, Val47]-thymopoietin II (32-49) on the low E-rosette forming capacity of cells from the aged patient with chronic renal failure was also compared with that of the synthetic thymopoietin II (32-49). The [Gln38, Thr43, Val47]-thymopoietin II (32-49) was approximately equipotent with the synthetic thymopoietin II (32-49) at a concentration of 100 μg/ml.

  十八肽H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH，对应于牛胸腺生成素II修订后的氨基酸序列的第32至49位，通过三个片段(32-36)、(37-41)和(42-49)的叠氮化物缩合合成，随后在茴香硫醚-邻甲酚存在下用氢氟酸脱保护。体外添加合成的胸腺生成素II(32-49)显著恢复了来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力至正常水平。[Gln38, Thr43, Val47]胸腺生成素II(32-49)对来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力的影响也与合成的胸腺生成素II(32-49)进行了比较。在100 μg/ml的浓度下，[Gln38, Thr43, Val47]胸腺生成素II(32-49)与合成的胸腺生成素II(32-49)大致等效。
• CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics
  作者：T. M. Vishwanatha、N. Narendra、Vommina V. Sureshbabu

  DOI：10.2174/092986612799363172

  日期：2012.3.1

  One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click reaction to efficient, practical and column-free preparation of the title compounds. The utility of the resulting unnatural amino acids as building blocks to prepare triazole possessing peptidomimetics is also delineated.

  Nα-Boc-溴甲基酮、NaN3和丙炔酸的一锅点击化学反应以良好至优异的产率提供了N-Boc保护的1,4-二取代1,2,3-β-酮三唑酸。使用CuI作为催化剂和DMSO作为溶剂使得点击反应变得高效、实用且无需柱层析即可制备标题化合物。还阐述了所得非天然氨基酸作为构建模块制备含三唑的类肽的实用性。
• Curtin–Hammett and Steric Effects in HOBt Acylation Regiochemistry
  作者：Benjamin D. Brink、Justin R. DeFrancisco、Julie A. Hillner、Brian R. Linton

  DOI：10.1021/jo200346r

  日期：2011.7.1

  While hydroxybenzotriazole is commonly used in a variety of bond-forming reactions, its acylation has been shown to produce a regiochemical (O vs N) mixture with complex kinetic behavior. Increased steric bulk on the electrophile favors formation of the oxygen-acylated product. Upon standing as a solid, the mixture can isomerize completely to the nitrogen adduct. An equilibrium ratio of regioisomers

  尽管羟基苯并三唑通常用于各种形成键的反应中，但已表明其酰化作用会产生具有复杂动力学行为的区域化学混合物（O对N）。亲电试剂上增加的空间体积有利于氧酰化产物的形成。静置为固体后，混合物可以完全异构化为氮加合物。通过添加亲核试剂或亲电试剂，可以在溶液中重新建立区域异构体的平衡比，这表明混合物的组成对随后的反应性并不重要。溶剂可以通过科廷-汉米特效应来影响这种区域化学平衡，其中极性溶剂中HOBt的互变异构平衡的偏移会将反应偏向氧加合物。