N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester | 125760-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester
• 英文别名: Fmoc-Thr-OPac；phenacyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxybutanoate
• CAS: 125760-27-2
• 化学式: C₂₇H₂₅NO₆
• 分子量: 459.499
• InChiKey: FLSCFYIUFWADFU-NSYGIPOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester 在 四氮唑 、 溶剂黄146 、 间氯过氧苯甲酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 Fmoc-Thr(PO(OBzl)OH)-OH
  参考文献：
  名称：

  Preparations ofN^α-Fmoc-O-[(Benzyloxy)hydroxyphosphinyl]β-Hydroxyα-Amino Acid Derivatives

  摘要：

  制备了 Nα-Fmoc-O-[(苄氧基)羟基膦酰基]丝氨酸和 Nα-Fmoc-O-[(苄氧基)羟基膦酰基]苏氨酸，以便根据 Fmoc 模式预磷酸化策略用于合成含磷丝氨酸或磷苏氨酸的肽。这些衍生物为结晶化合物，有利于用作固相法自动多肽合成的构建模块。

  DOI：

  10.1246/bcsj.69.465
• 作为产物：
  描述：

  Fmoc-Thr-OH 、 2-溴苯乙酮 在 三乙胺 、 二环己胺 作用下， 生成 N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester
  参考文献：
  名称：

  Preparations ofN^α-Fmoc-O-[(Benzyloxy)hydroxyphosphinyl]β-Hydroxyα-Amino Acid Derivatives

  摘要：

  制备了 Nα-Fmoc-O-[(苄氧基)羟基膦酰基]丝氨酸和 Nα-Fmoc-O-[(苄氧基)羟基膦酰基]苏氨酸，以便根据 Fmoc 模式预磷酸化策略用于合成含磷丝氨酸或磷苏氨酸的肽。这些衍生物为结晶化合物，有利于用作固相法自动多肽合成的构建模块。

  DOI：

  10.1246/bcsj.69.465

文献信息

• Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis
  作者：Peter M. Fischer

  DOI：10.1016/s0040-4039(00)60836-5

  日期：——

  The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one-pot procedure from N(alpha)-Fmoc (9-fluorenylmethoxycarbonyl) and N(alpha)-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives. The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains after peptide chain assembly, desirable, e.g., for phosphorylation or glycosilation.
• Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen
  作者：Sergei A. Svarovsky、Zoltan Szekely、Joseph J. Barchi

  DOI：10.1016/j.tetasy.2004.12.003

  日期：2005.1

  Herein we describe the synthesis gold nanoshells encapsulated with up to 90 units of the Thomsen-Friedenreich (TF) tumor-associated carbohydrate antigen (TACA) disaccharide (Galbeta1-3GaINAc-alpha-O-Ser/Thr) as well as the assembly of a suitably linked designer glycopeptide as a precursor to similar multivalent presentations on gold. The TF-coated nanoparticles are highly stable, water soluble, and easily handled. Improvements in the linker technology used to attach the disaccharide to the particles led to a robust multivalent platform for the presentation of this important carbohydrate. The antigen retains all recognition characteristics while displayed on this template as shown by several in vitro assays. This area of research could lead to the development of novel therapeutic agents that inhibit protein-carbohydrate interactions. Published by Elsevier Ltd.
• Synthesis of TN and T Antigen Glycopeptide Sequences of tumor-associated MUC-1 usingS-pent-4-enyl thioglycosides
  作者：Michael Leuck、Horst Kunz

  DOI：10.1002/prac.19973390160

  日期：——

  The syntheses of glycopeptides 34 and 38 with tumor associated T-N and T antigen structure containing a partial sequence of the tandem repeat unit of the polymorphic epithelial mucin MUC-1 were achieved via fragment condensations. Electrophilic activation of S-pent-4-enyl thioglycosides was applied for the construction of O-glycosyl amino acid and saccharide building blocks.
• Steric Control of N-Acetylgalactosamine In Glycosidic Bond Formation
  作者：J Yule

  DOI：10.1016/00404-0399(50)1442k-

  日期：1995.9.18

  N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of rx-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable for commercial production of mucin type glycopeptides with O-linked carbohydrate structures which are currently being investigated as vaccines against cancers.
• Chemical synthesis of analogs of the glycopeptide contulakin-G, an analgetically active conopeptide from Conus geographus
  作者：Ulrika Westerlind、Thomas Norberg

  DOI：10.1016/j.carres.2005.11.010

  日期：2006.1

  Cone snails are marine predators that use immobilizing venoms for catching prey. Chemical analysis of the venoms has revealed a variety of biologically active small and intermediate size peptides rich in post-translational modifications (modified amino acids, glycosylation). The glycopeptide contulakin-G(pGlu-Ser-Glu-Glu-Gly-Gly-Ser-Asn-Ala-[beta-D-Galp-(1 -> 3)-alpha-D-GalpNAc(I ->]Thr-Lys-Lys-Pro-Tyr-Ile-Leu-OH) is a potent analgesic from Conus geographus venom. The in vivo activity of synthetic contulakin-G was previously found to be significantly higher compared to that of a peptide lacking the glycan. In order to further investigate the importance of the glycan, we have now synthesized analogs of contulakin-G where the glycan chain O-linked to threonine has been altered either to beta-D-Galp-(1 -> 3)-P-D-GalpNAc-, alpha-D-Galp-(1 -> 3)-alpha-D-GalpNAc-, or beta-D-Galp-(1 -> 6)-alpha-D-GalP-NAc-. The glycopeptides were assembled on a Wang resin using commercially available Fmoc amino acids and synthetically prepared Fmoc-protected threonine derivatives carrying O-acetyl protected sugar chains. The final products were thoroughly characterized by NMR and mass spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.