193887-44-4

Basic information

• Product Name: FMOC-L-BETA-HOMOLEUCINE
• Synonyms: FMOC-LEU-(C*CH2)OH;FMOC-L-BETA-HOMOLEUCINE;FMOC-BETA-HOLEU-OH;FMOC-BETA-HOMOLEU-OH;(3S)-N-3-(9-FLUORENYLMETHOXYCARBONYL)-3-AMINO-5-METHYL-HEXANOIC ACID;(S)-3-(FMOC-AMINO)-5-METHYLHEXANOIC ACID;(S)-3-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-5-METHYL-HEXANOIC ACID;N-FMOC-3(S)-AMINO-5-METHYLHEXANOIC ACID
• CAS NO: 193887-44-4
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.44
• Product Categories: β-Homo Amino Acids;Beta amino acids;Unusual Amino Acids
• Mol File: 193887-44-4.mol

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 572.1 °C at 760 mmHg
• Flash Point: 299.8 °C
• Appearance: /
• Density: 1.189 g/cm³
• Vapor Pressure: 6.3E-14mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• PKA: 4.40±0.10(Predicted)
• BRN: 7723942
• CAS DataBase Reference: FMOC-L-BETA-HOMOLEUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-BETA-HOMOLEUCINE(193887-44-4)
• EPA Substance Registry System: FMOC-L-BETA-HOMOLEUCINE(193887-44-4)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 193887-44-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

Fmoc-l-beta-homoleucine

InChI:InChI=1/C22H25NO4/c1-14(2)11-15(12-21(24)25)23-22(26)27-13-20-18-9-5-3-7-16(18)17-8-4-6-10-19(17)20/h3-10,14-15,20H,11-13H2,1-2H3,(H,23,26)(H,24,25)/t15-/m0/s1

Upstream product

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

Downstream Products

• 1010820-69-5 C₃₅H₅₂BrN₅O₈ 
• 1010820-76-4 C₂₈H₃₉BrN₄O₇ 
• 1010820-70-8 C₃₇H₄₈BrN₅O₈ 
• 1188890-03-0 C₄₁H₆₆N₆O₁₀ 

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