H-Ala-Gly-OBzl | 66285-47-0

• 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-Ala-Gly-OBzl
• 英文别名: L-Alanylglycin-benzylester；benzyl 2-[[(2S)-2-aminopropanoyl]amino]acetate
• CAS: 66285-47-0
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: KEMPYSFDOHLRAH-VIFPVBQESA-N

物化性质

• 沸点：
  410.6±30.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

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-Ala-Gly-OBzl 在 钯 氢气 作用下， 以 水 、 溶剂黄146 、 叔丁醇 为溶剂， 生成 L-丙氨酰甘氨酸
  参考文献：
  名称：

  N-羧基α-氨基酸酐与α-氨基酸酯逐步反应的位阻

  摘要：

  研究了 4-烷基恶唑烷二酮 (1) (N-羧基 α-氨基酸酐 (NCAs)) 与 α-氨基酸苄酯对甲苯磺酸酯 (2) 在低温和室温下在含三乙胺的乙腈中的反应机理。观察到两种类型的反应：（1）NCAs 的聚合反应是用少量的 2 引发的，产生多肽（6），（2）二肽苄酯（4）是通过 NCAs 与酯类。聚合和二肽形成 (1+2) 似乎都是由酯的氨基对 NCA 的 C-5 碳的亲核攻击引发的。当氨基酸酯 (R2) 的侧链比 NCA (R1) 的侧链更大时，聚合进行。相反，

  DOI：

  10.1246/bcsj.54.2705
• 作为产物：
  描述：

  Boc-Ala-Gly-OBzl 在 三氟乙酸 作用下， 反应 1.5h， 生成 H-Ala-Gly-OBzl
  参考文献：
  名称：

  Synthesis of a Partial Sequence of Proinsulin Using the A-Chain of Natural Insulin. III. Synthesis of a Peptide Corresponding to Positions 41–81 of Bovine Proinsulin

  摘要：

  为了合成牛前胰岛素，使用了与天然牛胰岛素A链的S-磺酸盐合成的Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A链的S-磺酸盐，其对应于牛前胰岛素的位置53–81，并将其与Boc–Ala–Leu–Glu(OBut)–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–N3偶联。在去除所得物质的保护基团后，对应于牛前胰岛素位置41–81的Ala–Leu–Glu–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A链的S-磺酸盐，通过在QAE-Sephadex A-25上的色谱法进行纯化。

  DOI：

  10.1246/bcsj.53.197

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。
• Synthesis of Rat Parathymosin .ALPHA. Fragment 1-28 and Examination of Its Inhibitory Activity towards the Restoring Activity of Thymosin .ALPHA.1 on the Impaired T-Lymphocytes of Uremic Patients.
  作者：Takashi ABIKO、Hiroshi SEKINO

  DOI：10.1248/cpb.39.2647

  日期：——

  A fragment corresponding to N-terminal octaeicosapeptide of rat parathymosin α was synthesized by assembling 5 peptide fragments, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole (molar ratio 1 : 1) in trifluoroacetic acid in the presence of dimethylselenium. Incubation of impaired T-lymphocytes isolated from uremic patients with the synthetic parathymosin α fragment 1-28 showed no immunological restoring effect, but when it was administered together with thymosin α1 it appeared to suppress the restoring effect of the thymosin α1 on the impaired T-lymphocytes of uremic patients.

  在二甲基硒存在下，将 5 个肽片段组合在一起，然后在三氟乙酸中用 1 M 三氟甲磺酸-硫代苯甲醚（摩尔比 1:1）进行脱保护，合成了与大鼠副胸腺肽 α 的 N 端八位二肽相对应的片段。用合成的副胸腺肽α片段 1-28 培养从尿毒症患者体内分离出来的受损 T 淋巴细胞，结果显示它没有免疫恢复作用，但当它与胸腺肽α1 一起使用时，似乎会抑制胸腺肽α1 对尿毒症患者受损 T 淋巴细胞的恢复作用。
• Stereoselective and N-terminal selective α-alkylation of peptides using a pyridoxal model compound as a chiral N-terminal activator
  作者：Kazuyuki Miyashita、Hiroshi Iwaki、Kuninori Tai、Hidenobu Murafuji、Takeshi Imanishi

  DOI：10.1039/a805596c

  日期：——

  Stereoselective and N-terminal selective α-alkylation of peptides is achieved using a pyridoxal model compound as an N-terminal activator which also functions as a chiral auxiliary.

  使用吡哆醛模型化合物作为 N 端激活剂（也可作为手性助剂）实现肽的立体选择性和 N 端选择性 α-烷基化。
• Phosphoramidate peptide inhibitors of human skin fibroblast collagenase
  作者：Zbigniew P. Kortylewicz、Richard E. Galardy

  DOI：10.1021/jm00163a044

  日期：1990.1

  An extensive series of N-(monoethylphosphoryl)peptides was synthesized and their inhibition of purified human skin fibroblast collagenase examined. At the cleavage site S1 all reported compounds have the (EtO)(OK)P(O) group and the peptide side chain extended toward the C-terminal end (up to P5') of the substrate sequence. These phosphoramidates with a tetrahedrally hybridized phosphorus atom are thought to be transition state analogue inhibitors. They exhibited fair inhibitory potency against this vertebrate collagenase having Ki values in the micromolar range. The most potent of these, (EtO)(OK)P(O)-Ile-TrpNHCH3 (68), inhibits with a Ki value of 1.5 microM and is nearly 100 times stronger than (EtO)(OK)P(O)-Ile-Ala-GlyOK (51) (Ki of 140 microM), which has the sequence matching that of the alpha 1 (I) chain of collagen in P1', P2', P3' after the cleavage site. Several compounds were prepared in an attempt to identify the nature of the S2', S3', and S4' binding sites. Alanine at the P2' position was replaced by leucine, phenylalanine, tryptophan, or tyrosine derivatives, resulting in Ki values in a significantly lower range, 1.0-40 microM, compared to 51. No upper size limitation or specificity has been found at this position, yet similar replacements at the P3' position, which is occupied naturally by a glycine residue, gave weaker inhibitors: (EtO)(OK)P(O)-Ile-Tyr(OBzl)-PheOK (57) had a Ki of 120 microM. Hexapeptide derivatives had weaker activities in the 270 microM-2 mM range. All inhibitors were evaluated by using the synthetic thio peptolide spectrophotometric assay.