benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate | 167319-89-3

• 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: benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate
• 英文别名: (S)-2-benzyloxycarbonylamino-5-hydroxypentanoic acid benzyl ester；2(S)-2-(benzyloxycarbonylamino)-5-hydroxyvaleric acid benzyl ester；(S)-N-Cbz-2-amino-5-hydroxyvaleric acid benzyl ester；(S)-benzyl 2-(N-benzyloxycarbonyl)amino-5-hydroxypentanoate；5-hydroxy-N-[(phenylmethoxy)carbonyl]-L-norvaline benzyl ester；5-hydroxy-N-[(phenylmethoxy)carbonyl]-L-norvaline；benzyl (2S)-5-hydroxy-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 167319-89-3
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: GXTKHEAAKHSSNT-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate 在 吡啶 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成
  参考文献：
  名称：

  由一种独特的肼形成酶底物制成的天然二氢哒嗪酮支架

  摘要：

  含氮-氮键的官能团很少见，但它们存在于相当广泛的天然产物中。最近对此类官能团的生物合成路线的澄清揭示了分布在整个细菌界中被忽视的生物合成基因，突出了尚未鉴定的具有特殊官能团的天然产物的存在。在这里，针对独特的肼形成基因的基因组挖掘方法导致了放线菌哒嗪酮 A ( 1 ) 和 B ( 2 ) 的发现)，第一个具有二氢哒嗪酮环的天然产物。Actinopyridazinone A 的结构是通过全合成明确建立的。生物合成研究揭示了源自该 N-N 键形成酶家族的天然肼的结构多样性。

  DOI：

  10.1021/jacs.2c05269
• 作为产物：
  描述：

  L-谷氨酸-5-甲酯 在 sodium hydroxide 、 锂硼氢 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 生成 benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate
  参考文献：
  名称：

  Insecticidal properties of some derivatives of L-canavanine

  摘要：

  The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production. The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue.

  DOI：

  10.1021/jf00058a034

文献信息

• Promoting peptide α-helix formation with dynamic covalent oxime side-chain cross-links
  作者：Conor M. Haney、Matthew T. Loch、W. Seth Horne

  DOI：10.1039/c1cc12010g

  日期：——

  Covalent side-chain cross-linking has been shown to be a viable strategy to control peptide folding. We report here that an oxime side-chain linkage can elicit α-helical folds from peptides in aqueous solution. The bio-orthogonal bridge is formed rapidly under neutral buffered conditions, and the resulting cyclic oximes are capable of dynamic covalent exchange.

  共价侧链交联已被证明是控制多肽折叠的一种可行策略。我们在此报告，在水中，通过肟侧链连接可以诱导多肽形成α螺旋折叠。这种生物正交桥在中性缓冲条件下迅速形成，并且所产生的环状肟能够进行动态共价交换。
• Preparation of Amino- and Carboxy-ProtectedL-α-Amino-ω-iodocarboxylic Acids
  作者：Johnny Easmon、Gottfried Heinisch、Wolfgang Holzer、Barbara Matuszczak

  DOI：10.1002/ardp.19953280414

  日期：——

  The synthesis of L‐α‐amino‐ω‐iodobutyric, valeric, and caproic acid esters protected at the amino function by a benzyloxycarbonyl group is reported.

  据报道，L-α-氨基-ω-碘丁酸酯、戊酸酯和己酸酯的合成在氨基官能团处被苄氧羰基保护。
• Synthesis of a Homologous Series of Side-Chain-Extended Orthogonally Protected Aminooxy-Containing Amino Acids
  作者：Terrence Burke Jr.、Fa Liu、Joshua Thomas

  DOI：10.1055/s-2008-1078600

  日期：2008.8

  Practical methodology is reported for the synthesis of a homologous series of side chain extended amino acids containing aminooxy functionality bearing orthogonal protection suitable for Fmoc peptide synthesis. These reagents may be useful for the preparation of libraries containing fragments joined by peptide linkers.

  报道了合成一系列同源侧链延伸氨基酸的实用方法，该氨基酸包含具有正交保护的氨基氧基官能团，适用于 Fmoc 肽合成。这些试剂可用于制备包含由肽接头连接的片段的文库。
• Design and Concise Synthesis of Fully Protected Analogues of <scp>l</scp>-γ-Carboxyglutamic Acid
  作者：Sheng Jiang、Peng Li、Christopher C. Lai、James A. Kelley、Peter P. Roller

  DOI：10.1021/jo061037q

  日期：2006.9.1

  The design and synthesis of four nonnaturally occurring amino acid analogues of l-γ-carboxyglutamic acid (Gla), appropriately protected for Fmoc-based solid-phase peptide synthesis (SPPS), is described. These amino acids are Bu-Mal 2, BCAH 3, Pen-Mal 4, and Cm-Gla 5. These Gla analogues have been designed to replace the glutamic acid of position 1 in the cyclic decapeptide G1TE, which is a potent inhibitor

  的设计与四个非天然存在的氨基酸类似物合成升- γ羧基谷氨酸（GLA），适当保护的用于基于Fmoc的固相肽合成（SPPS），进行说明。这些氨基酸是Bu-Mal 2，BCAH 3，Pen-Mal 4和Cm-GLA 5。这些GLA类似物已被设计成取代环状十肽G1TE中位置1的谷氨酸，环状十肽G1TE是酪氨酸激酶的有效抑制剂，以进一步增强与信号转导受体的Grb2-SH2结构域的结合。在新的氨基酸中，Glu的丙酸侧链已被丙二酰基或羧甲基丙二酰基部分所取代，该部分位于距α-碳不同距离处，以优化Grb2-SH2结构域的磷酸酪氨酸结合腔中的相互作用。另外，已经开发了适于大规模生产的制备Fmoc保护的1 -γ-羧基谷氨酸的直接有效的合成路线，以55％的总产率提供了这种重要且独特的氨基酸1。
• Facile New Method for Preparation of Optically Active Protected Proline
  作者：Jun-ichi Yamaguchi、Masaaki Ueki

  DOI：10.1246/cl.1996.621

  日期：1996.8

  Treatment of L-N-protected 2-amino-5-bromopentanoic acid ester, which was prepared from protected L-glutamic acid, with sodium hydride in tetrahydrofuran (THF) proceeded to give the corresponding protected L-proline in high yield. On the other hand, the reaction of 2-aminobutyric acid derivative with sodium hydride gave the 1-aminocyclopropane-1-carboxylic acid derivative.

  用四氢呋喃 (THF) 中的氢化钠处理由受保护的 L-谷氨酸制备的 LN 保护的 2-氨基-5-溴戊酸酯，以高产率得到相应的保护 L-脯氨酸。另一方面，2-氨基丁酸衍生物与氢化钠反应得到1-氨基环丙烷-1-羧酸衍生物。