Z-Ser-N3 | 41446-15-5

• 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-Ser-N3
• 英文别名: N-benzyloxycarbonyl-L-seryl azide；N-Benzyloxycarbonyl-L-serylazid；benzyl N-[(2S)-1-azido-3-hydroxy-1-oxopropan-2-yl]carbamate
• CAS: 41446-15-5
• 化学式: C₁₁H₁₂N₄O₄
• 分子量: 264.241
• InChiKey: UMNJUYXVVGCCFA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Ser-N3 在 sodium hydroxide 、 乙醚 、 乙酸乙酯 作用下， 生成 Z-L-Seryl-L-methionin
  参考文献：
  名称：

  Understanding nanoindentation unloading curves

  摘要：

  实验表明，使用伯克维奇三角锥形压头获得的纳米压痕卸载曲线通常可以用幂律关系 P = α（h - hf）m 很好地描述，其中 hf 是完全卸载后的最终深度，α 和 m 是材料常数。然而，幂律指数并不像锥形压头（m = 2）或扁圆冲头（m = 1）的弹性接触那样固定为一个整数值，而是在 m = 1.2-1.6 的范围内因材料而异。根据对刚性锥体压入弹塑性材料的有限元模拟观察，建立了一个简单的模型，为这种行为提供了物理解释。该模型基于一个具有 "有效形状 "的压头的概念，其几何形状由压入过程中形成的塑性硬度印痕的形状决定。通过该模型，可以将幂律关系中的材料常数与弹性模量和硬度等更基本的材料特性联系起来。本文提出了一些简单的论点，根据这些论点，可以从压头下的压力分布推导出有效压头形状。

  DOI：

  10.1557/jmr.2002.0386
• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酰肼 在 盐酸 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 Z-Ser-N3
  参考文献：
  名称：

  氨基酸和多肽。二十五。通过固相和常规溶液法将新开发的β-1-和β-2-金刚烷酸天冬氨酸酯用于肽合成。

  摘要：

  新开发的β-1-和β-2-金刚烷酰基天冬氨酸[H-Asp（O-1-Ada）-OH和H-Asp（O-2-Ada）-OH]用于合成C端八肽常规溶液法制备人绒毛膜促性腺激素（hCG）的β-亚基，固相法测定胰岛素受体的α-亚基（30-55）的六糖肽，目的是抑制合成过程中天冬酰胺的形成天冬氨酰肽。证实1-Ada和2-Ada基团对于Asp残基的β-羧基功能是有用的保护基。

  DOI：

  10.1248/cpb.37.2209

文献信息

• Amino Acids and Peptides. XXXVII. Synthesis of Stereoisomeric Nonapeptides Corresponding to Sequence 41-49 of Eglin c and Examination of Their Inhibitory Activity against Human Leukocyte Cathepsin G and .ALPHA.-Chymotrypsin.
  作者：Ayumi FUJII、Satoshi TSUBOI、Keiichi ASADA、Yoko NAGAMATSU、Junichiro YAMAMOTO、Yoshio OKADA

  DOI：10.1248/cpb.42.1518

  日期：——

  A nonapeptide, H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OH, corresponding to sequence 41-49 of eglin c inhibited leukocyte cathepsin G and α-chymotrypsin with Ki values of 2.2×10-5 and 7.2×10-6M, respectively, although eglin c itself inhibited leukocyte elastase, cathepsin G and α-chymotrypsin with Ki values of 6.0×10-9, 5.5×10-9 and 2.5×10-9M, respectively. The inhibitory activity of the nonapeptide decreased following incubation with cathepsin G due to the cleavage of the Leu45-Asp46 peptide bond. Therefore, Leu45 and/or Asp46 were replaced with D-amino acids and the inhibitory activities of the resultant nonapeptides were examined. Their inhibitory activities against cathepsin G and α-chymotrypsin were much weaker than those of the all-L-type nonapeptide, suggesting that the amino acids at the active site, Leu45 and Asp46 are required to be in the L-configuration for potent activity.

  一种非apeptide，H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OH，对应于eglin c序列41-49，分别以2.2×10-5和7.2×10-6M的Ki值抑制白细胞组织蛋白酶G和α-胰凝乳蛋白酶，尽管eglin c本身分别以6.0×10-9、5.5×10-9和2.5×10-9M的Ki值抑制白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶。非apeptide的抑制活性在与组织蛋白酶G孵育后下降，这是由于Leu45-Asp46肽键的断裂。因此，Leu45和/或Asp46被替换为D-氨基酸，并对产生的非apeptide的抑制活性进行了检查。它们对组织蛋白酶G和α-胰凝乳蛋白酶的抑制活性远弱于所有L型非apeptide，表明活性位点上的氨基酸，Leu45和Asp46，需要处于L-构型才能发挥强大活性。
• Amino acids and peptides. XXVIII. Synthesis of peptide fragments related to eglin c and studies on the relationship between their structure and effects on human leukocyte elastase, cathepsin G and .ALPHA.-chymotrypsin.
  作者：Satoshi TSUBOI、Kazunori NAKABAYASHI、Yoshikazu MATSUMOTO、Naoki TENO、Yuko TSUDA、Yoshio OKADA、Yoko NAGAMATSU、Junichiro YAMAMOTO

  DOI：10.1248/cpb.38.2369

  日期：——

  Various peptide fragments related to eglin c, which consists of 70 amino acid residues, were synthesized by a conventional solution method and their inhibitory effects on leukocyte elastase, cathepsin G and α-chymotrypsin were examined. Among them, H-Arg-Glu-Tyr-Phe-OMe (eglin c 22-25) and H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe (eglin c 41-49) inhibited cathepsin G and α-chymotrypsin but not leukocyte elastase, while H-Thr-Asn-Val-Val-OMe (eglin c 60-63) inhibited leukocyte elastase but not cathepsin G or α-chymotrypsin, although eglin c potently inhibited leukocyte elastase, cathepsin G and α-chymotrypsin. These results indicated that the interaction sites of eglin c with leukocyte elastase, cathepsin G and α-chymotrypsin might be different.

  采用常规的溶液法合成了与来自家蚕血淋巴的抗蛋白酶eglin c（由70个氨基酸残基构成）相关的各种肽片段，并检验了它们对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的抑制效应。其中，H-Arg-Glu-Tyr-Phe-OMe（eglin c 22-25）和H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe（eglin c 41-49）能抑制组织蛋白酶G和α-胰凝乳蛋白酶，但不能抑制白细胞弹性蛋白酶，而H-Thr-Asn-Val-Val-OMe（eglin c 60-63）能抑制白细胞弹性蛋白酶，但不能抑制组织蛋白酶G或α-胰凝乳蛋白酶，尽管eglin c对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶都具有强抑制作用。这些结果提示，eglin c与白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的相互作用部位可能各不相同。
• <scp>L</scp>-SERYLGLYCYLGLYCINE
  作者：Erich Baer、Jonas Maurukas、Donald D. Clarke

  DOI：10.1139/v56-155

  日期：1956.9.1

  A synthesis of the hitherto unreported L-serylglycylglycine by two different methods is described. N-carbobenzoxy L-serylglycylglycine benzyl ester, an intermediate in the preparation of the tripeptide, was found to be a suitable derivative in the synthesis of L-α-phosphatidyl L-serylglycylglycine.

  描述了通过两种不同方法合成迄今尚未报道的L-丝氨酰甘氨酰甘氨。在三肽制备过程中的中间体N-羧苄氧基L-丝氨酰甘氨苄酯被发现是合成L-α-磷脂酰L-丝氨酰甘氨的合适衍生物。
• Amino acids and peptides. XIV Synthesis and biological activity of three S-peptide analogues of bovine pancreatic ribonuclease A (RNase A).
  作者：NAOKI TENO、SATOSHI TSUBOI、TOMOKO SHIMAMURA、YOSHIO OKADA、YOSHIMI YANAGIDA、MAKIKO YOSHINAGA、KAZUKO OHGI、MASACHIKA IRIE

  DOI：10.1248/cpb.35.468

  日期：——

  Three S-peptide analogues of bovine pancreatic ribonuclease A (RNase A), [Nle1] [Lys7] S-peptide (I), [Lys1] [Nle7] S-peptide (II) and [Nle1] [Nle7] S-peptide (III), were synthesized by the fragment condensation method and their ability to reactivate S-protein was examined. It was found that Lys1 and Lys7 both have roles in the reactivation of S-protein.

  采用片段缩合法合成了牛胰腺核糖核酸酶 A（RNase A）的三种 S 肽类似物，即 [Nle1] [Lys7] S 肽（I）、[Lys1] [Nle7] S 肽（II）和 [Nle1] [Nle7] S 肽（III），并考察了它们重新激活 S 蛋白的能力。结果发现，Lys1 和 Lys7 都在 S 蛋白的再活化过程中发挥作用。
• Human chorionic gonadotropin. VI. Synthesis of a tetratriacontapeptide corresponding to the C-terminal sequence 112-145 of the .BETA.-subunit of human chorionic gonadotropin (hCG).
  作者：YOSHIO OKADA、KOICHI KAWASAKI、SHIN IGUCHI、MASAMI YAGYU、KENJI YAMAJI、TETSU TAKAGI、NAGATOSHI SUGITA、OSAMU TANIZAWA

  DOI：10.1248/cpb.29.2851

  日期：——

  The tetratriacontapeptide corresponding to sequence 112-145 of the β-subunit of human chorionic gonadotropin (hCG) was synthesized by assembling peptide fragments by the azide procedure, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). New Zealand white rabbits were immunized with the conjugated antigen in Freund's complete adjuvant. Antiserum capable of 30% specific binding of 125I-hCG or 125I-β-subunit of hCG at a dilution of 1 : 5000 was produced.

  通过叠氮法组装肽片段，然后经反式脂肪酸处理和催化氢化，合成了对应于人绒毛膜促性腺激素（hCG）β亚基序列 112-145 的四三位一体肽。该肽与牛血清白蛋白（BSA）共轭。新西兰白兔在弗罗因德完全佐剂中接合抗原进行免疫。在 1 : 5000 的稀释度下，产生的抗血清能与 125I-hCG 或 hCG 的 125I-β 亚基产生 30% 的特异性结合。