D-aspartic acid benzyl ester | 79337-40-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天冬氨酸类衍生物
• 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: D-aspartic acid benzyl ester
• 英文别名: D-Asparaginsaeure-α-monobenzylester；1-Benzyl D-Aspartate；(3R)-3-amino-4-oxo-4-phenylmethoxybutanoic acid
• CAS: 79337-40-9
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: NJSRYBIBUXBNSW-SECBINFHSA-N

物化性质

• 熔点：
  176 °C
• 沸点：
  391.0±37.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  D-aspartic acid benzyl ester 在 三溴化磷 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 54.0h， 生成 C₁₂H₁₁NO₄S
  参考文献：
  名称：

  具有确定结构的聚β肽的水不敏感合成。

  摘要：

  具有生物相容性和耐蛋白水解性的聚β肽具有广泛的应用，并且通过强力的LiN（SiMe3）催化，在手套箱中或通过Schlenk线通过苛刻且对水敏感的β-内酰胺开环聚合反应合成。 2。我们开发了一种可控且对水不敏感的β-氨基酸N-硫代羧基酸酐（β-NTA）开环聚合反应，该反应可在开放容器中操作，以高收率制备具有多种官能团，可变的聚β-肽链长，分散度窄和定义的架构。这些优点暗示了β-NTA聚合反应和所得的聚-β-肽的广泛应用，这被发现具有模仿HDP的具有有效抗菌活性的聚-β-肽所证实。活性β-NTA聚合可控制无规合成，

  DOI：

  10.1002/anie.202001697
• 作为产物：
  描述：

  N-叔丁氧羰基-D-天冬氨酸 1-苄酯 在 水 作用下， 反应 0.05h， 以100%的产率得到D-aspartic acid benzyl ester
  参考文献：
  名称：

  A mild Boc deprotection and the importance of a free carboxylate

  摘要：

  We report a facile and rapid removal of Boc protecting groups using microwave heating in H2O, With deprotection only requiring a free carboxylic acid group in the starting material. Unlike previous approaches, no additional reagents are required. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.09.027

文献信息

• ——
  作者：Matts Kågedahl、Peter W. Swaan、Carl T. Redemann、Mary Tang、Charles S. Craik、Francis C. Szoka, Jr.、Svein Øie

  DOI：10.1023/a:1012044526054

  日期：——

  human intestinal bile acid transporter to transport cholic acid conjugates with potential HIV-1 protease inhibitory activity. METHODS Cholic acid was conjugated at the 24 position of the sterol nucleus with various amino acids and amino acid analogs. The CaCo-2 cell line was used as a model to investigate the interaction of these bile acid conjugates with the human intestinal bile acid transporter. Interaction

  目的研究人肠胆汁酸转运蛋白转运具有潜在HIV-1蛋白酶抑制活性的胆酸结合物的能力。方法胆酸在固醇核的24位与各种氨基酸和氨基酸类似物结合。CaCo-2细胞系被用作模型来研究这些胆汁酸结合物与人肠道胆汁酸转运蛋白的相互作用。通过抑制牛磺胆酸的转运来定量载体和结合物之间的相互作用，并通过放射性标记的结合物在该细胞系中的转运来证实。结果当抑制牛磺胆酸转运时，与转运蛋白的最高相互作用发生在固醇核的24至29个区域周围存在单个负电荷时。第二个负电荷或正电荷显着降低了相互作用。牛磺胆酸抑制放射性标记的胆甾醇-L-Lys-ε-tBOC酯和胆甾醇-D-Asp-β-苄基酯的转运。在所有测试的化合物中，只有胆甾醇-D-Asp-β-苄基酯显示适度的HIV-1蛋白酶抑制活性，IC50为125 microM。结论具有适当立体化学的胆酸-氨基酸缀合物被人胆汁酸转运蛋白识别并转运，并显示出适度的HIV-1蛋白酶抑制活性
• Switchable Synthesis of 7‐ and 14‐Membered Cyclic Peptides Containing <i>N</i>‐Methyl‐ and β‐Amino Acids Utilizing Microflow Technology
  作者：Shinichiro Fuse、Ren Okabe

  DOI：10.1002/ejoc.202300700

  日期：2023.9.14

  Switchable synthesis of 7- and 14-membered cyclic peptides containing non-proteinogenic amino acids was achieved. This is the first report that describes the synthesis of smaller cyclic N-methylated peptides via dimerization-cyclization strategy.

  实现了含有非蛋白氨基酸的7元和14元环肽的可切换合成。这是第一篇描述通过二聚-环化策略合成较小的环状N-甲基化肽的报告。
• Antibody-Catalyzed Rearrangement of a Peptide Bond: Mechanistic and Kinetic Investigations
  作者：Louis J. Liotta、Richard A. Gibbs、Scott D. Taylor、Patricia A. Benkovic、Stephen J. Benkovic

  DOI：10.1021/ja00122a001

  日期：1995.5

  Catalysis of the deamidation of asparagine residues may provide a powerful method for the deactivation of proteins. Catalytic antibodies (Gibbs et al. Science 1992, 258, 803) have been induced that catalyze the deamidation of a model dipeptide through an intermediate succinimide. Investigations of the mechanistic characteristics of two such antibodies, RG2-23C7 and RG2-2E4, revealed their ability to accelerate the hydrolysis of either the R- or S-enantiomers of the succinimide by factors of 10-500-fold to yield differing ratios of the aspartate and isoaspartate products. The mixed product ratios imply that two tetrahedral binding sites of unequal effectiveness were induced in response to the tetrahedral mimics (a phosphinate or secondary hydroxyl) within the hapten structure. The antibody RG2-2E4 also catalyzes the deamidation of either the D- or L-asparagine within the dipeptide through the intermediate cyclic imide, resulting in a multistep reaction sequence featuring a series of tetrahedral transition states. pH-rate profiles do not implicate functional groups within the antibodies' combining sites for either the deamidation or hydrolytic reactions. The strategy of bifunctional or higher order transition state mimics should provide a route to developing catalytic antibodies for reactions requiring multistep processing.
• Acyclic analogs of lipid A: synthesis and biological activities.
  作者：Murty A. R. C. Bulusu、Peter Waldstaetten、Johannes Hildebrandt、Eberhard Schuetze、Gerhard Schulz

  DOI：10.1021/jm00097a003

  日期：1992.9

  The synthesis of a series of novel acyclic analogues of lipid A, the lipophilic terminal of lipopolysaccharide (LPS), is reported. In these compounds, the reducing glucose unit of lipid A has been replaced by an acyclic analogue unit (abbreviated as AAU) consisting of a spacer (of varying length), an (R)-3-hydroxytetradecanamido moiety (of varying configuration at the carbon of attachment), and a CO2H group. The AAU has been attached to the anomeric carbon of the nonreducing glucose unit of lipid A, either through glycosidic linkage or through an acyl linkage. Further, amide isosteres of these acyclic analogues have been prepared using suitably protected 2,3-diamino-2,3-dideoxyglucose instead of 2-amino-2-deoxyglucose. All the compounds were well characterized and were tested for their ability to induce TNF-alpha in mouse bone marrow-derived macrophages, to enhance nonspecific resistance to infection in mice and to induce endotoxic shock in mice. The results showed a dramatic dependence, for the first time, on the length of the spacer and on the configuration of the carbon bearing the amido group in the AAU part of the analogues.
• <b>Glutamic and Aspartic Anhydrides. Rearrangement of N-Carboxyglutamic 1,5-Anhydride to the Leuchs' Anhydride and Conversion of the Latter to Pyroglutamic Acid</b>
  作者：J. Kovacs、H. Nagy. Kovacs、R. Ballina

  DOI：10.1021/ja00895a033

  日期：1963.6

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