Fmoc-d-Thr-OH

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-d-Thr-OH
• 英文别名: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutanoic acid
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: OYULCCKKLJPNPU-DFDFJRDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 Fmoc-d-Thr-OH 在 三氟化硼乙醚 作用下， 以 丙酮 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  肽合成中假脯氨酸作为单个氨基酸的范围和局限性

  摘要：

  受保护的 4-羧基恶唑烷和噻唑烷（假脯氨酸）是丝氨酸、苏氨酸或半胱氨酸氨基酸的衍生物。此类化合物与其他受保护的氨基酸一起用于肽合成。它们通常在肽序列在合成过程中容易聚集时使用，因为它们能够破坏二级结构的形成。这些化合物通常作为二肽应用。在目前的工作中，Fmoc 保护的假脯氨酸被合成并应用于肽合成，而不是作为二肽而是作为单个氨基酸。测试了不同的酰化方案和氨基酸以酰化假脯氨酸。合成了几种“困难”的肽以确认这种结构的功效。

  DOI：

  10.1007/s00726-021-02973-1
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 D-threonine 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以90%的产率得到Fmoc-d-Thr-OH
  参考文献：
  名称：

  肽合成中假脯氨酸作为单个氨基酸的范围和局限性

  摘要：

  受保护的 4-羧基恶唑烷和噻唑烷（假脯氨酸）是丝氨酸、苏氨酸或半胱氨酸氨基酸的衍生物。此类化合物与其他受保护的氨基酸一起用于肽合成。它们通常在肽序列在合成过程中容易聚集时使用，因为它们能够破坏二级结构的形成。这些化合物通常作为二肽应用。在目前的工作中，Fmoc 保护的假脯氨酸被合成并应用于肽合成，而不是作为二肽而是作为单个氨基酸。测试了不同的酰化方案和氨基酸以酰化假脯氨酸。合成了几种“困难”的肽以确认这种结构的功效。

  DOI：

  10.1007/s00726-021-02973-1

文献信息

• Parallel solid phase synthesis of tetrasubstituted diethylenetriamines via selective amide alkylation and exhaustive reduction of N-acylated dipeptides
  作者：Adel Nefzi、John M. Ostresh、Richard A. Houghten

  DOI：10.1016/s0040-4020(98)01043-6

  日期：1999.1

  Polyamines are a rapidly developing area of vital importance to biomedical science. Selective N-alkylation followed by N-terminal acylation and the complete reduction of carbonyl amide bonds enables the preparation by parallel solid phase synthesis of a wide range of N1,N5,1,4-tetrasubstituted-1,5-diamino-3-azapentane derivatives.

  多胺是对生物医学至关重要的快速发展领域。选择性的N-烷基化，接着通过N-末端酰化和的羰酰胺键的完全降低使得能够通过宽范围的N个并行固相合成制备1，N 5，1,4-四取代-1,5-二氨基-3- -氮杂戊烷衍生物。
• AMINO ACID GENERATOR AND POLYSILOXANE COMPOSITION CONTAINING THE SAME
  申请人：Kato Taku

  公开号：US20110073977A1

  公开（公告）日：2011-03-31

  There is provided an amino acid generator comprising a protecting group for an amino group that is eliminated to generate an amino acid, and a coating film forming composition using the amino acid generator and a polysiloxane composition containing the amino acid generator. A coating film forming composition comprising: a component (A): an amino acid generator comprising a protecting group that is eliminated to generate an amino acid, which is a compound of Formula (1): D-A (1) where D is a protecting group for an amino group, and A is an organic group remaining after subtracting hydrogen atoms from an amino group of an amino acid; a component (B): a hydrolyzable silane, a hydrolysis product thereof, a hydrolysis-condensation product thereof, or a mixture thereof; and a component (C): a solvent.
• US9257576B2
  申请人：——

  公开号：US9257576B2

  公开（公告）日：2016-02-09
• A Boron‐Dependent Antibiotic Derived from a Calcium‐Dependent Antibiotic
  作者：Shao‐Lun Chiou、Yi‐Ju Chen、Chu‐Ting Lee、Minh Ngoc Ho、Jiayuan Miao、Po‐Cheng Kuo、Cheng‐Chih Hsu、Yu‐Shan Lin、John Chu

  DOI：10.1002/anie.202317522

  日期：2024.1.25

  The prevalence of drug‐resistant bacterial pathogens foreshadows a healthcare crisis. Calcium‐dependent antibiotics (CDAs) are promising candidates to combat infectious diseases as many of them show modes of action (MOA) orthogonal to widespread resistance mechanisms. The calcium dependence is nonetheless one of the hurdles toward realizing their full potential. Using laspartomycin C (LspC) as a model, we explored the possibility of reducing, or even eliminating, its calcium dependence. We report herein a synthetic LspC analogue (B1) whose activity no longer depends on calcium and is instead induced by phenylboronic acid (PBA). In LspC, Asp1 and Asp7 coordinate to calcium to anchor it in the active conformation; these residues are replaced by serine in B1 and condense with PBA to form a boronic ester with the same anchoring effect. Using thin‐layer chromatography, MS, NMR, and complementation assays, we demonstrate that B1 inhibits bacterial growth via the same MOA as LspC, i.e., sequestering the cell wall biosynthetic intermediate undecaprenyl phosphate. B1 is as potent and effective as LspC against several Gram‐positive bacteria, including methicillin‐resistant Staphylococcus aureus and vancomycin‐resistant Enterococcus. Our success in converting a CDA to a boron‐dependent antibiotic opens a new avenue in the design and functional control of drug molecules.
• Scope and limitations of pseudoprolines as individual amino acids in peptide synthesis
  作者：Dmitry A. Senko、Nikita D. Timofeev、Igor E. Kasheverov、Igor A. Ivanov

  DOI：10.1007/s00726-021-02973-1

  日期：2021.5

  peptide synthesis not as dipeptides but as individual amino acids. Different acylation protocols and amino acids were tested to acylate pseudoprolines. Several “difficult” peptides were synthesized to confirm the efficacy of such constructions. It was shown that pseudoprolines could be easily synthesized and used in automated or manual synthesis not as dipeptides but as ordinary amino acids.

  受保护的 4-羧基恶唑烷和噻唑烷（假脯氨酸）是丝氨酸、苏氨酸或半胱氨酸氨基酸的衍生物。此类化合物与其他受保护的氨基酸一起用于肽合成。它们通常在肽序列在合成过程中容易聚集时使用，因为它们能够破坏二级结构的形成。这些化合物通常作为二肽应用。在目前的工作中，Fmoc 保护的假脯氨酸被合成并应用于肽合成，而不是作为二肽而是作为单个氨基酸。测试了不同的酰化方案和氨基酸以酰化假脯氨酸。合成了几种“困难”的肽以确认这种结构的功效。