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193887-45-5

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193887-45-5 Usage

Description

(S)-Fmoc-beta2-homoleucine is a specialized chemical compound that belongs to the category of amino acids and derivatives. It features the 'Fmoc' (Fluorenylmethyloxycarbonyl) protecting group, which is integral in peptide synthesis, as it shields the amino group from unwanted side reactions. This group can be easily removed when it is no longer required. The 'S' in its name indicates its stereochemistry, which is a specific spatial arrangement of atoms. The term 'beta2-homoleucine' refers to the uncommon amino acid analog of leucine that it represents, making (S)-Fmoc-beta2-homoleucine a unique and valuable compound in the fields of biochemistry and medicinal chemistry research.

Uses

Used in Biochemistry Research:
(S)-Fmoc-beta2-homoleucine is used as a research compound for studying the properties and interactions of amino acids and their derivatives. Its unique structure and the presence of the Fmoc protecting group make it a valuable tool in understanding peptide synthesis and related biochemical processes.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (S)-Fmoc-beta2-homoleucine is employed as a building block for the synthesis of novel peptides and peptide-based drugs. Its specific stereochemistry and the ability to incorporate it into peptide chains with controlled side reactions contribute to the development of potential therapeutic agents.
Used in Peptide Synthesis:
(S)-Fmoc-beta2-homoleucine is used as an amino acid component in the synthesis of peptides. The Fmoc protecting group allows for the stepwise construction of peptide chains, with the protection and deprotection of the amino group facilitating the controlled addition of each amino acid. This method is crucial for the synthesis of complex peptide structures with specific biological activities.
Used in Drug Development:
(S)-Fmoc-beta2-homoleucine may be utilized in the development of new drugs, particularly in the design of peptide-based therapeutics. Its unique properties and the ability to incorporate it into peptide sequences can lead to the creation of novel drug candidates with potential applications in various therapeutic areas.

Check Digit Verification of cas no

The CAS Registry Mumber 193887-45-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,3,8,8 and 7 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 193887-45:
(8*1)+(7*9)+(6*3)+(5*8)+(4*8)+(3*7)+(2*4)+(1*5)=195
195 % 10 = 5
So 193887-45-5 is a valid CAS Registry Number.

193887-45-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-4-methylpentanoic acid

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:193887-45-5 SDS

193887-45-5Downstream Products

193887-45-5Relevant articles and documents

Enantioselective H-atom transfer reactions: A new methodology for the synthesis of β2-amino acids

Sibi, Mukund P.,Patil, Kalyani

, p. 1235 - 1238 (2004)

A radical step: The addition of radicals to amino acrylates and subsequent H-atom transfer in the presence of chiral Lewis acid activators provides β2-amino acids in high yields and enantiomeric purity (see scheme; Ln* = chiral ligands, Fmoc = 9-fluorenylmethoxycarbonyl).

Enantioselective synthesis of beta-amino acids using hexahydrobenzoxazolidinones as chiral auxiliaries

Reyes-Rangel, Gloria,Jimenez-Gonzalez, Erika,Olivares-Romero, Jose Luis,Juaristi, Eusebio

experimental part, p. 2839 - 2849 (2009/06/18)

A practical synthetic route for the asymmetric synthesis of β2-amino acids is described. In the first step, the procedure involves the N-acylation of readily available, enantiopure hexahydrobenzoxazolidinone (4R,5R)-1 with 3-methylbutanoyl chloride 2, 4-methylpentanoic acid 3, and 3-(1-tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid 4 to afford derivatives 5a, 5b, and 5c, respectively, which were alkylated with high diastereoselectivity by means of reaction between their sodium enolates and benzyl bromoacetate. Removal of the chiral auxiliary from the alkylated products followed by hydrogenation and hydrolysis gave β2-amino acids (S)-10a, (S)-10b, and (S)-10c, which were N-protected with Fmoc. Enantiomeric (R)-10a-c were similarly prepared from the isomeric hexahydrobenzoxazolidinone (4S,5S)-1; thus, the route presented here provides access to both enantiomers of valuable highly enantioenriched β2-amino acids.

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

Guichard, Gilles,Abele, Stefan,Seebach, Dieter

, p. 187 - 206 (2007/10/03)

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!

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