212688-54-5

Basic information

• Product Name: Fmoc-D-beta-Homoleucine
• Synonyms: Fmoc-D-beta-Homoleucine;Fmoc-D-beta-HoLeu-OH;(R)-3-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-5-Methylhexanoic acid;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-β-homoleucine
• CAS NO: 212688-54-5
• Molecular Formula: C22H25NO4
• Molecular Weight: 367.4382
• Mol File: 212688-54-5.mol

Chemical Properties

• Boiling Point: 572.1±33.0 °C(Predicted)
• Appearance: /
• Density: 1.188±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.40±0.10(Predicted)
• CAS DataBase Reference: Fmoc-D-beta-Homoleucine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-D-beta-Homoleucine(212688-54-5)
• EPA Substance Registry System: Fmoc-D-beta-Homoleucine(212688-54-5)

Safety Data

• Hazardous Substances Data: 212688-54-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Fmoc-D-beta-Homoleucine is used as a building block for the construction of peptide chains, allowing researchers to create peptides with specific sequences and structures. This is crucial for the development of new drugs and therapeutic agents.
Used in Peptide Synthesis:
Fmoc-D-beta-Homoleucine is used as a key component in the synthesis of peptides, enabling the creation of complex and diverse peptide structures that can be tailored for specific applications.
Used in the Development of Peptidomimetic Compounds:
Fmoc-D-beta-Homoleucine is used as a starting material in the development of peptidomimetic compounds, which are designed to mimic the structure and function of natural peptides. These compounds often possess enhanced stability and pharmacological properties, making them valuable in drug discovery and development processes.
Used in Drug Discovery and Development:
Fmoc-D-beta-Homoleucine is used as a valuable tool in the drug discovery and development processes, due to its unique chemical properties and its role in the synthesis of peptides and peptidomimetic compounds. This allows researchers to explore new therapeutic avenues and create innovative treatments for various diseases and conditions.

Upstream product

• 103321-59-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride 
• 1001439-29-7 C₂₄H₂₇NO₆ 
• 35661-60-0 Fmoc-Leu-OH 
• 186581-53-3 diazomethane 
• 193954-24-4 (S)-(9H-fluoren-9-yl)methyl (1-diazo-5-methyl-2-oxohexan-3-yl)carbamate 

Downstream Products

• 1311394-86-1 (S)-β(2)hArg-Arg-Pro-Tyr-Ile-β(3)hLeu-OH 
• 1311394-85-0 (R)-β(2)hArg-Arg-Pro-Tyr-Ile-β(3)hLeu-OH 
• 1147129-82-5 C₁₁₅H₁₆₁N₁₇O₂₇S₂ 
• 1010820-70-8 C₃₇H₄₈BrN₅O₈ 
• 1010820-76-4 C₂₈H₃₉BrN₄O₇ 

Relevant articles and documents

Exceptionally simple homologation of protected α- to β-amino acids in the presence of silica gel

The Wolff rearrangement of α-amino acid-derived diazoketones is simply achieved by gentle warming in a ethyl acetate/silica gel slurry containing catalytic amounts of silver trifluoroacetate. Without workup (not counting filtration and evaporation) the pr

beta-peptides as catalysts: poly-beta-leucine as a catalyst for the Julia-Colonna asymmetric epoxidation of enones.

Poly-beta-leucines have been evaluated as catalysts for the Julia-Colonna asymmetric epoxidation of enones; the beta 3-isomer was found to be an effective catalyst for the epoxidation of chalcone (70% ee) and some analogues.

Convenient and simple synthesis of N-{[(9H-fluoren-9- yl)methoxy]carbonyl}-(Fmoc) protected β-amino acids (=homo-α-amino acids) employing Fmoc-α-amino acids and dicyclohexylcarbodiimide(DCC) mixtures

A simple approach for the homologation of α-amino acids to β-amino acids by the Arndt-Eistert method employing Fmoc-α-amino acid and N, N1- dicyclohexylcarbodiimide (DCC) mixture for the acylation of diazomethane, synthesizing the key intermediates Fmoc-α-amino acyldiazomethanes as crystalline solids is described.

Preparation of N-Fmoc-Protected β2- and β3-Amino Acids and Their Use as Building Blocks for the Solid-Phase Synthesis of β-Peptides

N-Fmoc-Protected (Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl) β-amino acids are required for an efficient synthesis of β-oligopeptides on solid support. Enantiomerically pure Fmoc-β3-amino acids (β3: side chain and NH2 at C(3)(=C(β))) were prepared from Fmoc-protected (S)- and (R)-α-amino acids with aliphatic, aromatic, and functionalized side chains, using the standard or an optimized Arndt-Eistert reaction sequence. Fmoc-β2-Amino acids (β2 side chain at C(2), NH2 at C(3)(=C(β))) configuration bearing the side chain of Ala, Val, Leu, and Phe were synthesized via the Evans' chiral auxiliary methodology. The target β3-heptapeptides 5-8, a β3- pentadecapeptide 9 and a β2-heptapeptide 10 were synthesized on a manual solid-phase synthesis apparatus using conventional solid-phase peptide synthesis procedures (Scheme 3). In the case of β3-peptides, two methods were used to anchor the first β-amino acid: esterification of the ortho-chlorotrityl chloride resin with the first Fmoc-β-amino acid 2 (Method I, Scheme 2) or acylation of the 4-(benzyloxy)benzyl alcohol resin (Wang resin) with the ketene intermediates from the Wolff rearrangement of amino-acid-derived diazo ketone 1 (Method II, Scheme 2). The former technique provided better results, as exemplified by the synthesis of the heptapeptides 5 and 6 (Table 2). The intermediate from the Wolff rearrangement of diazo ketones 1 was also used for sequential peptide-bond formation on solid support (synthesis of the tetrapeptides 11 and 12). The CD spectra of the β2- and β3-peptides 5, 9. and 10 show the typical pattern previously assigned to an (M) 31 helical secondary structure (Fig.). The most intense CD absorption was observed with the pentadecapeptide 9 (strong broad negative Cotton effect at ca. 213 nm); compared to the analogous heptapeptide 5, this corresponds to a 2.5 fold increase in the molar ellipticity per residue!

Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted wolff rearrangement

A highly efficient protocol for Amdt-Eistert chain elongation of the base-labile fluorenylmethoxycarbonyl (Fmoc) protected α-amino acids by Ag+- catalyzed, ultrasound-promoted Wolff rearrangement of the corresponding α- diazo ketones at room temperature is described. The enantiomeric purity of the products was examined by capillary zone electrophoresis with chiral buffer systems.

Convenient and stereospecific homologation of N-fluorenyl-methoxycarbonyl-α-amino acids to their β-homologues

A very simple approach to the enantioselective homologation of α-amino acids is presented which is based on the formation of N-Fmoc-aminoacyldiazomethanes with nearly quantitative yields and on the complete retention of both chiral configuration and N-ter