methoxybenzyloxycarbonyl-Thr | 47096-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methoxybenzyloxycarbonyl-Thr
• 英文别名: Moz-L-Thr；Z(OMe)-Thr-OH；Moz-Thr-OH；N-(p-Methoxybenzyloxycarbonyl)-L-threonin；(2S,3R)-3-hydroxy-2-[(4-methoxyphenyl)methoxycarbonylamino]butanoic acid
• CAS: 47096-14-0
• 化学式: C₁₃H₁₇NO₆
• 分子量: 283.281
• InChiKey: FDIAQXGUARMOMO-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methoxybenzyloxycarbonyl-Thr 在 Alcalase 、 水 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 为溶剂， 生成 Moz-L-Thr-L,D-Val-L-Leu-OMe
  参考文献：
  名称：

  Chemo-Enzymatic Synthesis of Optically Active Amino Acids and Peptides

  摘要：

  AbstractThe industrial alkaline protease, alcalase, is stable and active in a high concentration of organic solvents and useful as a biocatalyst for (i) diastereoselective hydrolysis of peptide esters and preparation of racemization‐free peptides; (ii) selective incorporation of esters of D‐amino acid into peptides in t‐butanol via a selective hydrolysis of esters of D,L‐amino acid, followed by using the unhydrolyzed D‐esters as a nucleophile in a kinetically controlled peptide bond formation; (iii) resolution of esters of amino acid in 95% t‐butanol/5% water, followed by saponification of the unreacted esters to offer both enantiomers with high yield and optical purity; (iv) completely resolve amino‐acid esters with high yield and optical purity via in situ racemization of the unreacted antipode catalyzed by pyridoxal 5‐phosphate; (v) cryobioorganic synthesis of peptides with increased yields 15%–40% of peptide bond formation by reaction at 5 °C instead of 25–30 °C of a kinetically controlled enzymatic reaction in alcohols.

  DOI：

  10.1002/jccs.199900046

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• Der 2.2.2‐Trifluor‐1‐benzyloxycarbonylamino‐äthyl‐Rest als Schutzgruppe für die Hydroxylgruppen des Serins und Threonins bei Peptidsynthesen
  作者：Friedrich Weygand、Wolfgang Steglich、Ferdinand Fraunberger、Piergiorgio Pietta、Jochen Schmid

  DOI：10.1002/cber.19681010323

  日期：1968.3

  Der 2.2.2-Trifluor-1-benzyloxycarbonylamino-äthyl-Rest ist zum Schutz der Hydroxylgruppen des Serins und Threonins hervorragend geeignet. Er ist durch Umsetzung von N-Acyl-aminosäure- oder N-Acyl-peptidderivaten mit 2.2.2-Trifluor-1-chlor-N-benzyloxycarbonyl-äthylamin leicht einführbar und läßt sich durch katalytische Hydrierung oder mit HBr/Eisessig bzw. HF wieder abspalten.

  2.2.2-三氟-1-苄氧基羰基氨基-乙基非常适合于保护丝氨酸和苏氨酸的羟基。它可以通过使N-酰基氨基酸或N-酰基肽衍生物与2.2.2-三氟-1-氯-N-苄氧基羰基乙胺反应而容易地引入，并可以通过催化氢化或与HBr /冰醋酸重新引入。高频分裂。
• Deacetyl-thymosin .ALPHA.1: Synthesis and immunological effect on lipoid nephrosis lymphocytes.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.30.1776

  日期：——

  We have replaced the Ac-Ser residue of bovine thymosin α1 (position 1) with Ser in order to examine the resulting change in immunological effect on the low resette-forming capacity with sheep erythrocytes of cells from a lipoid nephrosis patient. The deacetyl-thymosin α1 was synthesized by the solution method. For the synthesis of the protected octaeicosapeptide, five peptide fragments were prepared by the stepwise elongation method with N-ethoxycarbonyl-2-ethoxy-1, 2-dihydroquinoline as a coupling reagent. The condensations of the fragments were achieved by Rudinger's azide procedure. Finally, all protecting groups were removed by HF treatment followed by catalytic hydrogenation. The in vitro addition of the synthetic deacetyl-thymosin α1 at a dose of 100 μg/ml was able to restore the rosette-forming capaoity with sheep erythrocytes of lipoid nephrosis cells to normal levels. Our preparations of deacetyl-thymosin α1 and thymosin α1 were found to be equally active in cases of lipoid nephrosis.

  我们用 Ser 取代了牛胸腺肽 α1（第 1 位）的 Ac-Ser 残基，以研究由此产生的免疫学效应变化对类脂肾病患者细胞与绵羊红细胞的低重影形成能力的影响。脱乙酰胸腺肽α1是用溶液法合成的。在合成受保护的八胜肽时，使用 N-乙氧羰基-2-乙氧基-1，2-二氢喹啉作为偶联试剂，通过分步延伸法制备了五个肽段。片段的缩合是通过鲁丁格叠氮程序实现的。最后，通过 HF 处理去除所有保护基团，然后进行催化加氢。在体外添加剂量为 100 μg/ml 的合成脱乙酰胸腺肽 α1，可使类脂肾细胞的绵羊红细胞形成莲座的能力恢复到正常水平。我们制备的脱乙酰胸腺肽α1和胸腺肽α1在类脂性肾病病例中具有同样的活性。
• Composition containing a penem or carbapenem antibiotic
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0226304B1

  公开（公告）日：1991-08-28
• Chen, Shui-Tein; Chang, Chung-Ho; Wang, Kung-Tsung, Journal of Chemical Research, Miniprint, 1991, # 8, p. 1967 - 1975
  作者：Chen, Shui-Tein、Chang, Chung-Ho、Wang, Kung-Tsung

  DOI：——

  日期：——