170643-02-4

Basic information

• Product Name: FMOC-D-ALLO-THR(TBU)-OH
• Synonyms: FMOC-D-ALLO-THR(TBU)-OH;FMOC-D-ALLO-THREONINE(TBU)-OH;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-O-T-BUTYL-D-ALLO-THREONINE;O-(tert-Butyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-allothreonine;FMOC-D-All-Thr(tBu)-OH;(2R,3R)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-(tert-butoxy)butanoic acid;N-Fmoc-O-tert-butyl-D-allo-threonine;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Allo-Thr(tBu)-OH
• CAS NO: 170643-02-4
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.46
• Mol File: 170643-02-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 581.7±50.0 °C(Predicted)
• Appearance: White/Powder
• Density: 1.197
• PKA: 3.42±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-ALLO-THR(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-ALLO-THR(TBU)-OH(170643-02-4)
• EPA Substance Registry System: FMOC-D-ALLO-THR(TBU)-OH(170643-02-4)

Safety Data

• Hazardous Substances Data: 170643-02-4(Hazardous Substances Data)

Usage

General Description

FMOC-D-ALLO-THR(TBU)-OH is a chemical compound commonly used in the field of organic chemistry. The compound consists of an FMOC (9H-fluoren-9-ylmethoxycarbonyl) protective group attached to a D-allo-threonine (D-ALLO-THR) amino acid with a tert-butyl (TBU) group. FMOC-D-ALLO-THR(TBU)-OH is often employed as a building block in peptide synthesis and can be used to create peptides with specific sequences and properties. It is important in the development of pharmaceuticals and biochemical research due to its ability to create unique and tailored peptide structures. Additionally, it can be used to study the structure and function of proteins and enzymes within the body.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 119323-52-3 (2R,3R)-2-Amino-3-tert-butoxy-butyric acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 130674-54-3 (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine 

Downstream Products

• 1445907-66-3 C₃₂H₅₀N₆O₉S 
• 1310050-75-9 nobilamide B 
• 130674-54-3 (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine 

Relevant articles and documents

Asymmetric synthesis of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives proper for solid-phase peptide coupling

Practical new routes for preparation of (2S,3S)-3-Me-glutamine and (R)-allo-threonine derivatives, the key structural components of cytotoxic marine peptides callipeltin O and Q, suitable for the Fmoc-SPPS, were developed. (2S,3S)-Fmoc-3-Me-Gln(Xan)-OH was synthesized via Michael addition reactions of Ni (II) complex of chiral Gly-Schiff base; while Fmoc-(R)-allo-Thr-OH was prepared using chiral Ni (II) complex-assisted α-epimerization methodology, starting form (S)-Thr(tBu)-OH.

Total synthesis of the large non-ribosomal peptide polytheonamide B

Polytheonamide B is by far the largest non-ribosomal peptide known at present, and displays extraordinary cytotoxicity (EC50 =68 pg ml -1 , mouse leukaemia P388 cells). Its 48 amino-acid residues include a variety of non-proteinogenic d- and l-amino acids, and the absolute stereochemistry of these amino acids alternate in sequence. These structural features induce the formation of a stable β-strand-type structure, giving rise to an overall tubular structure over 30A? in length. In a biological setting, this fold is believed to transport cations across the lipid bilayer through a pore, thereby acting as an ion channel. Here, we report the first chemical construction of polytheonamide B. Our synthesis relies on the combination of four key stages: syntheses of non-proteinogenic amino acids, a solid-phase assembly of four fragments of polytheonamide B, silver-mediated connection of the fragments and, finally, global deprotection. The synthetic material now available will allow studies of the relationships between its conformational properties, channel functions and cytotoxicity.