L-丝氨酸(2,3,3-D3) | 105591-10-4

• 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
• 中文名称: L-丝氨酸(2,3,3-D3)
• 中文别名: L-丝氨酸-D3
• 英文名称: 2,3,3-[2H3]-L-serine
• 英文别名: (2S)-<2,3,3-(2)H3>serine；L-serine-2,3,3-d3；[2,3,3-D]L-serine；[2,3,3-²H]L-serine；(2,3,3-²H)-serine；[2,3,3-²H]-Ser；D-serine-2,3,3-d3；L-Serine (2,3,3-D3)；(2S)-2-amino-2,3,3-trideuterio-3-hydroxypropanoic acid
• CAS: 105591-10-4
• 化学式: C₃H₇NO₃
• 分子量: 108.07
• InChiKey: MTCFGRXMJLQNBG-RBXBQAPRSA-N

物化性质

• 熔点：
  >211°C (dec.)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-丝氨酸(2,3,3-D3) 以 水 为溶剂， 反应 30.0h， 生成 3,3-dideuterio-DL-serine
  参考文献：
  名称：

  丝氨酸八聚体反应：益生元相关性的指标。

  摘要：

  DOI：

  10.1002/anie.200351210
• 作为产物：
  描述：

  在 三溴化硼 、 氘 作用下， 生成 L-丝氨酸(2,3,3-D3) 、 (2S,3R)-<2,3-(2)H2>serine
  参考文献：
  名称：

  Ramer, Shawn E.; Moore, Richard N.; Vederas, John C., Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713

  摘要：

  DOI：

文献信息

• 10.1021/acs.jmedchem.4c00774
  作者：Li, Kaixuan、Gilberti, Alexa L.、Marden, Jocelyn A.、Akula, Hari K.、Pollard, Alyssa C.、Guo, Shuwen、Hu, Bao、Tonge, Peter J.、Qu, Wenchao

  DOI：10.1021/acs.jmedchem.4c00774

  日期：——

  To fully explore the potential of 18F-labeled l-fluoroalanine for imaging cancer and other chronic diseases, a simple and mild radiosynthesis method has been established to produce optically pure l-3-[18F]fluoroalanine (l-[18F]FAla), using a serine-derivatized, five-membered-ring sulfamidate as the radiofluorination precursor. A deuterated analogue, l-3-[18F]fluoroalanine-d3 (l-[18F]FAla-d3), was also

  为了充分探索18 F标记的l-氟丙氨酸在癌症和其他慢性疾病成像方面的潜力，建立了一种简单温和的放射合成方法来生产光学纯的l -3-[ 18 F]氟丙氨酸（ l -[ 18 F] FAla)，使用丝氨酸衍生的五元环磺酰胺作为放射性氟化前体。还制备了氘化类似物l -3-[ 18 F]氟丙氨酸-d 3 ( l -[ 18 F]FAla-d 3 )以提高代谢稳定性。 l -[ 18 F]FAla 和l -[ 18 F]FAla-d 3均被 9L/lacZ、MIA PaCa-2 和 U87MG 细胞快速摄取，并被证明是丙氨酸-丝氨酸-半胱氨酸的底物（ ASC) 氨基酸转运蛋白。在 U87MG 荷瘤小鼠中评估了l -[ 18 F]FAla、 l -[ 18 F]FAla-d 3和 d -对映体d -[ 18 F]FAla-d 3对肿瘤进行成像的能力。尽管l -[ 18 F]FAla 和l -[ 18 F]FAla-d
• Mechanistic Studies on the Substrate-Tolerant Lanthipeptide Synthetase ProcM
  作者：Subha Mukherjee、Wilfred A. van der Donk

  DOI：10.1021/ja504692v

  日期：2014.7.23

  Lanthipeptides are a class of post-translationally modified peptide natural products. They contain lanthionine (Lan) and methyllanthionine (MeLan) residues, which generate cross-links and endow the peptides with various biological activities. The mechanism of a highly substrate-tolerant lanthipeptide synthetase, ProcM, was investigated herein. We report a hybrid ligation strategy to prepare a series of substrate analogues designed to address a number of mechanistic questions regarding catalysis by ProcM. The method utilizes expressed protein ligation to generate a C-terminal thioester of the leader peptide of ProcA, the substrate of ProcM. This thioester was ligated with a cysteine derivative that resulted in an alkyne at the C-terminus of the leader peptide. This alkyne in turn was used to conjugate the leader peptides to a variety of synthetic peptides by copper-catalyzed azide alkyne cycloaddition. Using deuterium-labeled Ser and Thr in the substrate analogues thus prepared, dehydration by ProcM was established to occur from C-to-N-terminus for two different substrates. Cyclization also occurred with a specific order, which depended on the sequence of the substrate peptides. Furthermore, using orthogonal cysteine side-chain protection in the two semisynthetic peptide substrates, we were able to rule out spontaneous non-enzymatic cyclization events to explain the very high substrate tolerance of ProcM. Finally, the enzyme was capable of exchanging protons at the alpha-carbon of MeLan, suggesting that ring formation could be reversible. These findings are discussed in the context of the mechanism of the substrate-tolerant ProcM, which may aid future efforts in lanthipeptide engineering.
• Ramer, Shawn E.; Moore, Richard N.; Vederas, John C., Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
  作者：Ramer, Shawn E.、Moore, Richard N.、Vederas, John C.

  DOI：——

  日期：——
• Serine Octamer Reactions: Indicators of Prebiotic Relevance
  作者：Zoltan Takats、Sergio C. Nanita、R. Graham Cooks

  DOI：10.1002/anie.200351210

  日期：2003.8.4