161529-13-1

Basic information

• Product Name: FMOC-L-ALANINOL
• Synonyms: FMOC-(S)-2-AMINO-1-PROPANOL;FMOC-ALA-OL;FMOC-ALANINOL;FMOC-L-ALANINOL;N-FMOC-L-ALANINOL;N-ALPHA-FMOC-L-ALANINOL;N-(9-FLUORENYLMETHOXYCARBONYL)-L-ALANINOL;Fmoc-DL-Alaninol
• CAS NO: 161529-13-1
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.35
• EINECS: 1533716-785-6
• Product Categories: Amino Acids;Amino Alcohols;Fmoc-Amino acid series
• Mol File: 161529-13-1.mol

Chemical Properties

• Melting Point: 120 °C
• Boiling Point: 503.9 °C at 760 mmHg
• Flash Point: 258.5 °C
• Appearance: /Solid
• Density: 1.21 g/cm³
• Vapor Pressure: 5.66E-11mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: -15°C
• PKA: 11.48±0.46(Predicted)
• CAS DataBase Reference: FMOC-L-ALANINOL(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-ALANINOL(161529-13-1)
• EPA Substance Registry System: FMOC-L-ALANINOL(161529-13-1)

Safety Data

• Hazardous Substances Data: 161529-13-1(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C18H19NO3/c1-12(10-20)19-18(21)22-11-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,12,17,20H,10-11H2,1H3,(H,19,21)/t12-/m0/s1

Upstream product

• 2749-11-3 (S)-Alaninol 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 146346-88-5 methyl 2-(((9H-fluoren-9-yl)methoxy)carbonyl)aminopropanoate 
• 329308-96-5 (S)-(9H-fluoren-9-yl)methyl 1-azido-1-oxopropan-2-ylcarbamate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 73724-40-0 (S)-2,5-dioxopyrrolidin-1-yl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate 

Downstream Products

• 146803-41-0 N-(fluorenylmethyloxycarbonyl)-L-alaninal 

Relevant articles and documents

Improved Strategy for the Synthesis of the Anticancer Agent Culicinin D

The anticancer peptaibol culicinin D was synthesised via a newly developed pathway. This route included an improved attachment of a C-terminal amino acid alcohol building block to 2-chlorotrityl chloride resin. A model system utilising readily available Fmoc-alaninol as the substitute for the unusual APAE building block was developed to investigate the resin-loading by N-anchoring of the first C-terminal residue and an intramolecular O-N acyl shift. The use of both Fmoc SPPS and the crucial O-N acyl transfer afforded a C-terminal alcohol that enabled the synthesis of a library of five related peptaibols. This model system was then applied to the synthesis of culicinin D. The C-terminal APAE building block was anchored to 2-chlorotrityl chloride resin in 67 % loading yield using the optimised conditions, and culicinin D (6.31 mg, 4 %) was prepared by SPPS prior to peptide cleavage and O-N acyl shift. This synthetic strategy was also used to prepare a diastereomer of culicinin D containing the unnatural (S)-AHMOD amino acid. The anticancer agent Culicinin D, active against breast tumor cells, was synthesised on the solid phase. The resin loading was improved by attachment of first residue to solid-phase via the amine rather than the alcohol. After SPPS and cleavage, the peptide alcohol was formed via an intramolecular O-N transfer reaction. Successful synthesis of several culicinin D analogues demonstrated the feasibility of this new synthetic strategy.

Synthesis, solvatochromic properties, and dipole moments of Fmoc-l-alaninol

An efficient protocol for the activation of N-(9-Fluorenylmethoxycarbonyl)- l-alanine [Fmoc-Ala-OH] employing 1-[(1-(cyano-2-ethoxy-2-oxoethylideneaminooxy) -dimethylamino-morpholinomethylene)] methanaminium hexa-fluorophosphate [COMU] and its reduction into (9H-fluoren-9-yl)methyl 1-hydroxypropan-2-ylcarbamate [Fmoc-l-alaninol] using sodium borohydride has been described. The method is trouble-free, quick and free from racemization. Fmoc-l-alaninol was characterized by 1H and 13C NMR, and mass spectral studies. The electronic absorption and fluorescence emission spectra of Fmoc-l-alaninol have been studied in solvents of different polarities, and the data were used to study the solvatochromic properties. The spectral variations were analyzed by the linear solvation energy relationship concept to visualize the nature and extent of solvent-solute interactions. Experimental values of ground-(μg) and excited-state (μe) dipole moments of Fmoc-l-alaninol were calculated by the solvatochromic shift method, and theoretical μg values were evaluated by quantum chemical calculations using Gaussian 03 and Chem3D Ultra 8.0. The higher value of excited-state dipole moment than the ground-state value indicates a substantial redistribution of π-electron densities in a more polar excited-state. Also, fluorescence emission peak undergoes a hypsochromic shift with increase in the polarity of the solvent, confirming n → π* transition.

Synthetic Lugdunin Analogues Reveal Essential Structural Motifs for Antimicrobial Action and Proton Translocation Capability

Lugdunin, a novel thiazolidine cyclopeptide, exhibits micromolar activity against methicillin-resistant Staphylococcus aureus (MRSA). For structure–activity relationship (SAR) studies, synthetic analogues obtained from alanine and stereo scanning as well as peptides with modified thiazolidine rings were tested for antimicrobial activity. The thiazolidine ring and the alternating d- and l-amino acid backbone are essential. Notably, the non-natural enantiomer displays equal activity, thus indicating the absence of a chiral target. The antibacterial activity strongly correlates with dissipation of the membrane potential in S. aureus. Lugdunin equalizes pH gradients in artificial membrane vesicles, thereby maintaining membrane integrity, which demonstrates that proton translocation is the mode of action (MoA). The incorporation of extra tryptophan or propargyl moieties further expands the diversity of this class of thiazolidine cyclopeptides.

COMPOUNDS AS BCL-2-SELECTIVE APOPTOSIS-INDUCING AGENTS

Provided are certain Bcl-2 inhibitors, pharmaceutical compositions thereof, and methods of use thereof.

PEPTIDE NUCLEIC ACID (PNA) MONOMERS WITH AN ORTHOGONALLY PROTECTED ESTER MOIETY

This application pertains to orthogonally protected esters of peptide nucleic acid (PNA) monomers, which ester groups can be removed under conditions that permit typical backbone and side chain acid- and base-labile protecting groups to remain substantially intact thereby permitting the high yield of PNA monomer carboxylic acids that are suitable for use in PNA oligomer synthesis. Exemplary ester groups include, but are not limited to, 2,2,2-trichloroethyl (TCE), 2,2,2-tribromoethyl (TBE), 2-bromoethyl (2-BE) and 2-iodoethyl groups (2-IE). This invention also pertains to novel methods for the synthesis of Backbone Ester compounds and related Backbone Ester Acid Salts.

Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library

A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino ac

Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3

A simple, rapid, and eco-friendly method for NaBH4 reduction of carboxylic acids to alcohols under solvent-free conditions was developed using a combination of 2,4,6-trichloro-1,3,5-triazine (TCT) with a catalytic amount of triphenylphosphine as an acid activator. With the 1 : 0.2 : 1.5 : 2 mole ratio of TCT : PPh3 : K2CO3 : NaBH4, carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids (Fmoc, Z) could readily undergo reduction to give the corresponding alcohols in good to excellent yields within 10 min.

An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator

A simple and efficient method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propane phosphonic acid cyclic anhydride (T3P) and subsequent reduction of the intermediate phosphonic anhydride with NaBH4 yield the alcohol in excellent yields with good purity in less duration. Reduction of several alkyl/aryl carboxylic acids and Nα-protected amino acids/peptide acids as well as Nβ-protected amino acids was successfully carried out to obtain corresponding alcohols in good yields and the products characterized. The procedure is mild, safe, simple and the isolation of the products is easy.

MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols

A facile, efficient and racemization-free method for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals. This method is found to be compatible with Fmoc-, Boc- and other side-chain protecting groups.