(gammaS,4S)-4-羧基-gamma-[[芴甲氧羰基]氨基]-2,2-二甲基-delta-氧代-3-恶唑烷戊酸叔丁酯 | 909115-33-9

• 物质功能分类: 生物化工 - 生化试剂
• 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: (gammaS,4S)-4-羧基-gamma-[[芴甲氧羰基]氨基]-2,2-二甲基-delta-氧代-3-恶唑烷戊酸叔丁酯
• 中文别名: (GAMMAS,4S)-4-羧基-GAMMA-[[芴甲氧羰基]氨基]-2,2-二甲基-DELTA-氧代-3-恶唑烷戊酸叔丁酯
• 英文名称: Fmoc-L-Glu(Ot-Bu)-L-Ser(Ψ^Me,MePro)-OH
• 英文别名: Fmoc-Glu-Ser(Ψ^Me,MePro)-OH；Fmoc-Glu(OtBu)-Ser(ψMe,Mepro)-OH；Fmoc-Glu(OtBu)-Ser(Psi(Me,Me)pro)-OH；(4S)-3-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid
• CAS: 909115-33-9
• 化学式: C₃₀H₃₆N₂O₈
• 分子量: 552.624
• InChiKey: DSGXIRQTDFOKPQ-ZEQRLZLVSA-N

物化性质

• 沸点：
  759.9±60.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• WGK Germany：
  2
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

简介

(GAMMAS，4S)-4-羧基-Gamma-[[芴甲氧羰基]氨基]-2，2-二甲基-Delta-氧代-3-恶唑烷戊酸叔丁酯可用于固相制备促胰液素（Secretin）。促胰液素是一种由十二指肠和空肠上段粘膜中的S细胞分泌的具有螺旋结构的碱性多肽，由27个氨基酸组成。它具有调节胰腺外分泌、抑制胃酸分泌和胃运动等多种生理功能。

生物活性

Fmoc-Glu(OtBu)-Ser(psi(Me,Me)pro)-OH 是一种二肽。

反应信息

• 作为反应物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 (gammaS,4S)-4-羧基-gamma-[[芴甲氧羰基]氨基]-2,2-二甲基-delta-氧代-3-恶唑烷戊酸叔丁酯 、 Fmoc-O-叔丁基-L-谷氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Fmoc-Val-Ala-Ala-Leu-Glu(OtBu)-Ser(ψMe,Mepro)-Glu(OtBu)-OH
  参考文献：
  名称：

  Coiled Coil Peptides as Universal Linkers for the Attachment of Recombinant Proteins to Polymer Therapeutics

  摘要：

  We have designed, synthesized, and characterized peptides containing four repeats of the sequences VAALEKE (peptide E) or VAALKEK (peptide K). While the peptides alone adopt in aqueous solutions a random coil conformation, their equimolar mixture forms heterodimeric coiled coils as confirmed by CD spectroscopy. S-Azidopentanoic acid was connected to the N-terminus of peptide E via a short poly(ethylene glycol) spacer. The terminal azide group enabled conjugation of the peitide with a synthetic drug carrier based on the N-(2-hydrokypropyl)methacrylamide copolymer containing propargyl groups using "click" chemistry. When incorporated into the polymer drug carrier, peptide E formed a stable noncovalent complex with peptide K beloning to a recombinant single-chain fraginent (scFv) of the M75 antibody. The complex thereby mediates a noncovalent linkage between the polymer drug carrier and the protein. The recombinant scFv antibody fragment was selected as a targeting ligand against carbonic anhydrase IX-a marker overexpressed by tumor cells of various human carcinomas. The antigen binding affinity of the polymer-scFv complex was confirmed by ELISA. This approach offers a well-defined, specific, and nondestructive universal method for the preparation of protein (antibody)-targeted polymer drug and gene carriers designed for cell-specific delivery.

  DOI：

  10.1021/bm200897b

文献信息

• Coiled Coil Peptides as Universal Linkers for the Attachment of Recombinant Proteins to Polymer Therapeutics
  作者：Michal Pechar、Robert Pola、Richard Laga、Karel Ulbrich、Lucie Bednárová、Petr Maloň、Irena Sieglová、Vlastimil Král、Milan Fábry、Ondřej Vaněk

  DOI：10.1021/bm200897b

  日期：2011.10.10

  We have designed, synthesized, and characterized peptides containing four repeats of the sequences VAALEKE (peptide E) or VAALKEK (peptide K). While the peptides alone adopt in aqueous solutions a random coil conformation, their equimolar mixture forms heterodimeric coiled coils as confirmed by CD spectroscopy. S-Azidopentanoic acid was connected to the N-terminus of peptide E via a short poly(ethylene glycol) spacer. The terminal azide group enabled conjugation of the peitide with a synthetic drug carrier based on the N-(2-hydrokypropyl)methacrylamide copolymer containing propargyl groups using "click" chemistry. When incorporated into the polymer drug carrier, peptide E formed a stable noncovalent complex with peptide K beloning to a recombinant single-chain fraginent (scFv) of the M75 antibody. The complex thereby mediates a noncovalent linkage between the polymer drug carrier and the protein. The recombinant scFv antibody fragment was selected as a targeting ligand against carbonic anhydrase IX-a marker overexpressed by tumor cells of various human carcinomas. The antigen binding affinity of the polymer-scFv complex was confirmed by ELISA. This approach offers a well-defined, specific, and nondestructive universal method for the preparation of protein (antibody)-targeted polymer drug and gene carriers designed for cell-specific delivery.