N-Z-D-threonine benzyl ester | 85995-50-2

• 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: N-Z-D-threonine benzyl ester
• 英文别名: benzyl (2R,3S)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 85995-50-2
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: VBKUVUJWFDXTMS-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Z-D-threonine benzyl ester 在 三氟化硼乙醚 、 氢溴酸 、 溶剂黄146 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-2-Benzyloxycarbonylamino-5-[(R)-1-((1R,2R)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

  摘要：

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00280-4
• 作为产物：
  描述：

  溴甲苯 、 N-苄氧羰基-D-苏氨酸 在 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以50%的产率得到N-Z-D-threonine benzyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative

  摘要：

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.

  DOI：

  10.1021/jm900598m

文献信息

• Carbon-13 NMR spectroscopy, a useful tool to determine the enantiomeric purity of synthetic threonine-containing glycopeptides. Spectra of diastereoisomeric .alpha.- and .beta.-D-galactopyranosyl-L- and D-threonine and -L- and -D-allothreonine
  作者：A. A. Pavia、J. M. Lacombe

  DOI：10.1021/jo00163a028

  日期：1983.7
• O-(Substituted)-α-amino-β-hydroxybutyric Acids
  作者：DONALD L. ROSS、CHARLES G. SKINNER、WILLIAM SHIVE

  DOI：10.1021/jo01092a014

  日期：1959.10
• Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives
  作者：Ahmad Ali Shaik、Sharmeen Nishat、Peter R. Andreana

  DOI：10.1021/acs.orglett.5b00512

  日期：2015.6.5

  A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to alpha- or beta-anomers in excellent yields (72-96%) and selectivity (similar to 100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.
• 191. Cyto-active amino-acids and peptides. Part VII. Derivatives of serine and threonine
  作者：F. Bergel、Roy Wade

  DOI：10.1039/jr9590000941

  日期：——
• Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative
  作者：Masazumi Iwashita、Kumiko Makide、Taro Nonomura、Yoshimasa Misumi、Yuko Otani、Mayuko Ishida、Ryo Taguchi、Masafumi Tsujimoto、Junken Aoki、Hiroyuki Arai、Tomohiko Ohwada

  DOI：10.1021/jm900598m

  日期：2009.10.8

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.