Fmoc-Val-Aib-OH | 128422-18-4

• 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: Fmoc-Val-Aib-OH
• 英文别名: Fmoc-Val-Aib；2-[(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylbutanamido]-2-methylpropanoic acid；2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]-2-methylpropanoic acid
• CAS: 128422-18-4
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: FHLCNIWPARVFGK-FQEVSTJZSA-N

物化性质

• 熔点：
  195-197 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  676.5±45.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Val-Aib-OH 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.5h， 生成 Boc-Trp-Ile-Ala-Aib-Ile-Val-Aib-Leu-Aib-Ψ(CS)-Pro-OMe
  参考文献：
  名称：

  Synthesis of Endothiopeptides and Their Cyclization to 1,3-Thiazol-5(4H)-imines

  摘要：

  Further investigations of the synthesis of endothio analogues of the segment 1-10 (8) of an apolar analogon of zervamicin IIA are described. The endothiodecapeptide Boc-Trp-Ile-Ala-Aib-Ile-Val-Aib-Leu-Aib-Psi(CS)-Pro-OMe (10) has been prepared in good yield by our novel methodology. On the other hand, all attempts to prepare endothio analogues of 8 with the thioamide group at position 3 (Ala') gave not the expected linear endothiopeptides but led to epimerized 1,3-thiazol-5(4H)-imine derivatives as the main products. The mixture of epimers of the thiazolimines 27, 30, and 31 have been separated by means of preparative HPLC, and their structures have been established by 2D-NMR experiments.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1899::aid-hlca1899>3.0.co;2-m
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl 1-{(2S)-2-methyl-1-[({1,1-dimethyl-2-[methyl(phenyl)amino]-2-oxoethyl}amino)carbonyl]propyl}carbamate 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 Fmoc-Val-Aib-OH
  参考文献：
  名称：

  Synthesis of Endothiopeptides and Their Cyclization to 1,3-Thiazol-5(4H)-imines

  摘要：

  Further investigations of the synthesis of endothio analogues of the segment 1-10 (8) of an apolar analogon of zervamicin IIA are described. The endothiodecapeptide Boc-Trp-Ile-Ala-Aib-Ile-Val-Aib-Leu-Aib-Psi(CS)-Pro-OMe (10) has been prepared in good yield by our novel methodology. On the other hand, all attempts to prepare endothio analogues of 8 with the thioamide group at position 3 (Ala') gave not the expected linear endothiopeptides but led to epimerized 1,3-thiazol-5(4H)-imine derivatives as the main products. The mixture of epimers of the thiazolimines 27, 30, and 31 have been separated by means of preparative HPLC, and their structures have been established by 2D-NMR experiments.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1899::aid-hlca1899>3.0.co;2-m

文献信息

• Synthesis of Peptides Containing ?,?-Disubstituted ?-Amino Acids by the Azirine/Oxazolone Method: The (12-20)-Nonapeptide of the Ionophore Alamethicin
  作者：Peter Wipf、Heinz Heimgartner

  DOI：10.1002/hlca.19900730103

  日期：1990.1.31

  The (12–20)-nonapeptide Z-Leu-Aib-Pro-Val-Aib-Aib-Glu (OBzl)-Gln-Pheol (10) of the ionophor alamethicin was synthesized by a new strategy, using 3-amino-2,2-dimethyl-2H-azirines 2 as synthons for the α-aminoisobutyric acid (Aib) moieties.

  用新的策略，使用3-氨基-2合成了ionophor alamethicin的（12–20）-九肽Z-Leu-Aib-Pro-Val-Aib-Aib-Glu（OBzl）-Gln-苯酚（10）作为α-氨基异丁酸（Aib）部分的合成子，2-2-二甲基-2 H -azirines 2。
• Facile synthesis of protected dipeptide acids containing C-terminal α,α-dialkyl amino acids.
  作者：Frank Bambino、Robert T.C. Brownlee、Francis C.K. Chiu

  DOI：10.1016/s0040-4039(00)92721-7

  日期：1991.7

  A facile synthesis is presented for a range of dipeptide units containing the conformationally restricted α,α-dialkyl amino acids. These dipeptide building blocks should be valuable in the synthesis of oligopeptides incorporating these units using Fmoc chemistry.

  对于一系列包含构象受限的α，α-二烷基氨基酸的二肽单元，提供了一种简便的合成方法。这些二肽结构单元在使用Fmoc化学合成包含这些单元的寡肽中应该是有价值的。
• Tantry, Subramanyam J.; Babu, Vommina V. Suresh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 6, p. 1282 - 1287
  作者：Tantry, Subramanyam J.、Babu, Vommina V. Suresh

  DOI：——

  日期：——
• Suresh Babu, Vommina V.; Ramana Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 11, p. 2328 - 2332
  作者：Suresh Babu, Vommina V.、Ramana Rao

  DOI：——

  日期：——
• WIPF, PETER;HEIMGARTNER, HEINZ, HELV. CHIM. ACTA, 73,(1990) N, C. 13-24
  作者：WIPF, PETER、HEIMGARTNER, HEINZ

  DOI：——

  日期：——