H-Gly-L-Ala-OBn | 46840-83-9

• 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: H-Gly-L-Ala-OBn
• 英文别名: Gly-Ala-OBzl；benzyl (2S)-2-[(2-aminoacetyl)amino]propanoate
• CAS: 46840-83-9
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: QDAJREIVNJGHAV-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Gly-L-Ala-OBn 生成 benzyl (2S)-2-[[2-[[(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetyl]amino]propanoate
  参考文献：
  名称：

  ZIMMERMANN, G.;HAAG, R.;STAHL, P.;SEIDEL, H.

  摘要：

  DOI：
• 作为产物：
  描述：

  H-Ala-OBzl 在 苯甲醚 、 三氟乙酸 作用下， 反应 4.0h， 生成 H-Gly-L-Ala-OBn
  参考文献：
  名称：

  肽的研究。CXIX。合成生长激素释放因子（hpGRF-40-OH）。

  摘要：

  通过在溶液中片段缩合，然后用三氟乙酸中的1M三氟甲磺酸-茴香硫醚去保护，合成了与生长激素释放因子(hpGRF-40-OH)的入口氨基酸序列相对应的十肽。在体内测定中，合成hpGRF-40-OH与合成hpGRF-44-NH2一样具有活性，但在体外测定中，合成hpGRF-40-OH的效力仅为合成hpGRF-44-NH2的36% 。

  DOI：

  10.1248/cpb.32.1193

文献信息

• Development of Supramolecular Organo-Gel Based on Tripeptide Skeletons
  作者：Eriko Azuma、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1248/cpb.58.680

  日期：——

  Boc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of antiparallel β-sheets through intermolecular hydrogen bonding was central to the generation of nanofibers during gelation.

  Boc-Ser-Val-Gly-OCH2Ph (31) 在芳香族溶剂中显示出强大的成胶能力，尤其是在甲苯中。31在甲苯中的最低成胶浓度为10 mg/ml，这意味着每分子三肽31固定了2500个甲苯分子。傅里叶变换红外光谱数据显示，通过分子间氢键形成反平行β-折叠是成胶过程中产生纳米纤维的关键。
• Introduction of 4(S)-oxazolidineacetic acid, 2-oxo (D-Oxac) motif in a polypeptide chain: synthesis and conformational analysis
  作者：Gianluigi Luppi、Marzia Villa、Claudia Tomasini

  DOI：10.1039/b210725m

  日期：2003.1.13

  A four step synthesis of 4(S)-oxazolidineacetic acid, 2-oxo benzyl ester (D-Oxac-OBn) from L-Asp-OH in 45% overall yield is reported. The formation of by-products is completely avoided, by microwave irradiation and by the use of caesium carbonate as base. Moreover the synthesis and IR and 1H NMR conformational analysis of the tetramers Boc-L-Val-D-Oxac-L-Ala-OBn and Boc-L-Val-D-Oxac-Aib-L-Ala-OBn in solution is reported.

  本研究以 L-Asp-OH 为原料，分四步合成了 4(S)-恶唑烷乙酸 2-氧代苄基酯（D-Oxac-OBn），总收率为 45%。通过微波辐照和使用碳酸铯作为碱，完全避免了副产物的生成。此外，还报道了四聚体 Boc-L-Val-D-Oxac-L-Ala-OBn 和 Boc-L-Val-D-Oxac-Aib-L-Ala-OBn 在溶液中的合成、红外和 1H NMR 构象分析。
• Development and Conformational Analysis of a Pseudoproline-Containing Turn Mimic
  作者：Gianluigi Luppi、Donato Lanci、Valerio Trigari、Marco Garavelli、Andrea Garelli、Claudia Tomasini

  DOI：10.1021/jo026233l

  日期：2003.3.1

  The liquid-phase synthesis and the conformational analysis of a small library of fully protected tetramers containing L-pyroglutamic acid (L-pGlu), (4S,5R)-4-methyl-5-carboxybenzyloxazolidin-2-one (L-Oxd), or (4R,5S)-4-methyl-5-carboxybenzyloxazolidin-2-one (D-Oxd) as residue i + 1 are reported to test the tendency of these oligomers to assume beta-hairpin conformation. The most promising molecule is BOC-L-Val-D-Oxd-Gly-L-Ala-OBn, which assumes a preferential beta-turn conformation in CDCl3, as shown by IR and H-1 NMR analysis. These findings have been confirmed by DFT calculations, which provide an interpretation for the available experimental data and agree with the reported observations.
• ZIMMERMANN, G.;HAAG, R.;STAHL, P.;SEIDEL, H.
  作者：ZIMMERMANN, G.、HAAG, R.、STAHL, P.、SEIDEL, H.

  DOI：——

  日期：——
• Studies on peptides. CXIX. Synthesis of growth hormone releasing factor (hpGRF-40-OH).
  作者：NOBUTAKA FUJII、MASANORI SHIMOKURA、HARUAKI YAJIMA、FUMIAKI SHONO、MASAFUMI TSUDA、AKIRA YOSHITAKE

  DOI：10.1248/cpb.32.1193

  日期：——

  The tetracontapeptide corresponding to the entrie amino acid sequence of growth hormone releasing factor (hpGRF-40-OH) was synthesized by fragment condensation in solution, followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. In in vivo assay, synthetic hpGRF-40-OH was as active as synthetic hpGRF-44-NH2, but in in vitro assay, the potency of synthetic hpGRF-40-OH was only 36% of that of synthetic hpGRF-44-NH2.

  通过在溶液中片段缩合，然后用三氟乙酸中的1M三氟甲磺酸-茴香硫醚去保护，合成了与生长激素释放因子(hpGRF-40-OH)的入口氨基酸序列相对应的十肽。在体内测定中，合成hpGRF-40-OH与合成hpGRF-44-NH2一样具有活性，但在体外测定中，合成hpGRF-40-OH的效力仅为合成hpGRF-44-NH2的36% 。