123639-61-2

Basic information

• Product Name: Fmoc-L-glutamic acid-gamma-benzyl ester
• Synonyms: N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-GLUTAMIC-ACID-GAMMA-BENZYL ESTER;N-(9-fluorenylmethoxycarbonyl)-L-glutamic acid-gamma-benzyl ester;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;Fmoc-L-glutamic acid γ-benzyl ester;L-Glutamicacid,N-[(9H-fluoren-9-ylmethoxy)carbon;N-9-Fluorenylmethyloxycarbonyl-L-glutamicacidg-benzylester
• CAS NO: 123639-61-2
• Molecular Formula: C₂₇H₂₅NO₆
• Molecular Weight: 459.49
• Product Categories: Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 123639-61-2.mol

Chemical Properties

• Melting Point: Decomposes
• Boiling Point: 698.2 ºC at 760 mmHg
• Flash Point: 376.1 ºC
• Appearance: White powder
• Density: 1.289 g/cm³
• Vapor Pressure: 1.83E-20mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: 2-8°C
• PKA: 3.70±0.10(Predicted)
• CAS DataBase Reference: Fmoc-L-glutamic acid-gamma-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-glutamic acid-gamma-benzyl ester(123639-61-2)
• EPA Substance Registry System: Fmoc-L-glutamic acid-gamma-benzyl ester(123639-61-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 123639-61-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Fmoc-L-glutamic acid-gamma-benzyl ester is used as a building block for the synthesis of various complex molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its incorporation into these molecules enhances their structural diversity and functional properties.
Used in Peptide Chemistry:
In the field of peptide chemistry, Fmoc-L-glutamic acid-gamma-benzyl ester serves as a crucial component in the solid-phase peptide synthesis (SPPS) process. It is used as a protected amino acid for the stepwise assembly of peptide chains, allowing for the efficient and controlled synthesis of peptides and proteins with desired sequences and functionalities.
Used in Pharmaceutical Industry:
Fmoc-L-glutamic acid-gamma-benzyl ester is utilized as a key intermediate in the development of novel drug candidates targeting various therapeutic areas. Its unique structure enables the design of peptides and peptidomimetics with improved pharmacokinetic properties, such as enhanced stability, bioavailability, and target selectivity.
Used in Research and Development:
In academic and industrial research settings, Fmoc-L-glutamic acid-gamma-benzyl ester is employed as a valuable tool for exploring the structure-activity relationships of peptides and proteins. It facilitates the synthesis of diverse peptide libraries, enabling the identification of potent and selective bioactive molecules with potential applications in drug discovery and development.

InChI:InChI=1/C27H25NO6/c29-25(33-16-18-8-2-1-3-9-18)15-14-24(26(30)31)28-27(32)34-17-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,23-24H,14-17H2,(H,28,32)(H,30,31)/t24-/m0/s1

Upstream product

• 57-88-5 cholesterol 

Downstream Products

• 123622-36-6 FMOC-Glu(OBn)-Cl 
• 157108-58-2 (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioic acid 5-benzyl ester 1-tert-butyl ester 
• 1036637-24-7 3-[N-(5-oxohexanoyl)-L-phenylalanyl-L-glutamyl-O-benzyl-L-phenylalanyl-L-glycine] 
• 1415218-38-0 C₆₃H₇₈N₁₀O₁₆ 
• 1639394-80-1 NH₂-Met-Glu(Bzl)-(7-amino-4-carbamoylmethylcoumarin) 
• 1558029-85-8 C₂₃H₂₃N₃O₆ 

Relevant articles and documents

A novel and efficient method for cleavage of phenacylesters by magnesium reduction with acetic acid

(Equation Presented) In the present study, we use magnesium turnings as a new deprotection reagent for the phenacyl group during orthogonal organic synthesis in the presence of other esters and sensitive protecting groups. By applying the new magnesium turnings/acetic acid deprotection method, phenacyl group can be more easily combined with other protecting groups that are not compatible with the zinc/acetic acid method.

PEPTIDE NUCLEIC ACID CONJUGATES

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Phosphate linked oligomers

Novel ethylene glycol compounds bearing various functional groups are used to prepare oligomeric structures. The ethylene glycol monomers can be joined via standard phosphate linkages including phosphorothioate, phosphodiester, and phosphoramidate linkages. Useful functional groups include nucleobases as well as polar groups, hydrophobic groups, ionic groups, aromatic groups and/or groups that participate in hydrogen-bonding.

Target-selective protocols based on mimics

A method to potentiate the effect of a chemotherapeutic agent in a tumor cell, which method comprises administering to said tumor cell, along with said chemotherapeutic agent, a potentiating amount of a compound of the formula: STR1 or an amide, ester or hybrid amide/ester thereof, wherein X is a hydrocarbon radical optionally substituted on any aromatic moiety contained therein; Y--CO is γ-Glu or β-Asp and AAC is an amino acid, preferably glycine, phenylglycine, β-alanine, alanine or phenylalanine is disclosed. Similar compounds can also be used to selectively exert cytotoxicity versus target cells as compared to nontarget cells and also to elevate the production of GM progenitors in bone marrow of mammalian subjects.

Pyrrolidine-containing monomers and oligomers

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Glutathione analogs and paralog panels comprising glutathione mimics

Compounds of the formula STR1 or the alkyl (1-6 C), alkenyl (1-6 C), or arylalkyl (7-12 C) amides or salts including the cycloamido forms thereof; wherein n is 1 or 2; wherein when n is 1, X is a mono- or disubstituted or unsubstituted hydrocarbyl (1-20 C) moiety optionally containing 1 or 2 nonadjacent heteroatoms (O, S or N), and wherein said substitution is selected from the group consisting of halo, OR, and SR, wherein R is H or lower alkyl (1-4 C); when n is 2, one X is as above defined and the other X is lower alkyl (1-4 C); Y is selected from the group consisting of STR2 wherein m is 1 or 2; and AAC is an amino acid coupled through a peptide bond to the remainder of the compound of formula 1, are useful as affinity ligands, elution reagents, solution inhibitors, diagnostic reagents and therapeutics. These compounds and analogous tripeptide glutathione analogs can be used as members of panels to obtain specific characteristic profiles for various glutathione-S-transferases.

Pyrrolidine-containing monomers and oligomers

Novel pyrrolidine monomers bearing various functional groups are used to prepare oligomeric structures. The pyrrolidine monomers can be joined via standard phosphate linkages including phosphodiester and phosphorothioate linkages. Useful functional groups include nucleobases as well as polar groups, hydrophobic groups, ionic groups, aromatic groups and/or groups that participate in hydrogen-bonding.

Glutathione analogs and paralog panels comprising glutathione mimics

Compounds of the formula or the alkyl (1-6C) or arylalkyl (7-12C) amides or salts including the cycloamido forms thereof;, wherein n is 1 or 2;, wherein when n is 1, X is a mono- or disubstituted or unsubstituted hydrocarbyl (1-20C) moiety optionally containing 1 or 2 nonadjacent heteroatoms (O, S or N), and wherein said substitution is selected from the group consisting of halo, OR, and SR, wherein R is H or lower alkyl (1-4C); when n is 2, one X is as above defined and the other X is lower alkyl (1-4C);, Y is selected from the group consisting of wherein m is 1 or 2; and, AACis an amino acid coupled through a peptide bond to the remainder of the compound of formula 1, are useful as affinity ligands, elution reagents, solution inhibitors, diagnostic reagents and therapeutics. These compounds and analogous tripeptide glutathione analogs can be used as members of panels to obtain specific characteristic profiles for various glutathione-S-transferases.