Z-Val-Aib | 66449-58-9

• 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: Z-Val-Aib
• 英文别名: 2-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoic acid
• CAS: 66449-58-9
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: GLDKDIZESDQPHU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  Z-Val-Aib 在 palladium on activated charcoal lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 氢气 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 50.17h， 生成
  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：

  benzyl N-{(1S)-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 Z-Val-Aib
  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

• Selektive Amidspaltung bei Peptiden mit ?,?-disubstituierten ?-Aminos�uren
  作者：Peter Wipf、Heinz Heimgartner

  DOI：10.1002/hlca.19870700213

  日期：1987.3.18

  Selective Amide Cleavage in Peptides Containing α,α-Disubstituted α-Amino Acids

  含α，α-二取代α-氨基酸的肽的选择性酰胺裂解
• 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。
• Kupplung von Peptiden mit C-terminalen ?,?-disubstituierten ? - Aminos�urenvia Oxazol-5(4H)-one
  作者：Peter Wipf、Heinz Heimgartner

  DOI：10.1002/hlca.19860690524

  日期：1986.7.30

  Peptide-Bond Formation with C-Terminal α,α-Disubstituted α - Amino Acids via Intermediate Oxazol-5(4H)-ones

  通过中间恶唑-5（4 H）-one与C末端α，α-二取代的α-氨基酸形成肽键
• Synthesis of Tripeptides Containing Heterocyclic α-Amino Acids by Using Heterospirocyclic 3-Amino-2H-azirines
  作者：Heinz Heimgartner、Christoph Strässler、Anthony Linden

  DOI：10.3987/com-18-s(t)22

  日期：——

  By using the 'azirine/oxazolone method', di- and tripeptides containing six-membered heterocyclic 4-amino-4-carboxylic acids with a piperidine, tetrahydropyran or tetrahydrothiopyran ring have been synthesized. It has been shown that the corresponding heterospirocyclic 3-(N-methyl-N-phenylamino)-2H-azirines are suitable synthons for these heterocyclic alpha-amino acids. As expected, the presence of these alpha,alpha-disubstituted alpha-amino acids stabilizes beta-turn conformations in the prepared tripeptides of type Z-Phe-Xaa-Val-OR.
• Efficient synthesis of alamethicin f-30 using a chloro imidazolidium coupling reagent, CIP
  作者：Kenichi Akaji、Yasunori Tamai、Yoshiaki Kiso

  DOI：10.1016/0040-4039(95)02023-i

  日期：1995.12

  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.