71989-18-9

Basic information

• Product Name: Fmoc-L-glutamic acid 5-tert-butyl ester
• Synonyms: N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-TERT-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-TERT-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-GLUTAMIC-ACID-GAMMA-T-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-GAMMA-T-BUTYL-L-GLUTAMIC ACID;N-FMOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-FMOC-O-T-BUTYL-L-GLU
• CAS NO: 71989-18-9
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.47
• EINECS: 276-253-8
• Product Categories: Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series;Pyridines
• Mol File: 71989-18-9.mol

Chemical Properties

• Melting Point: 83-90 °C
• Boiling Point: 638.1 °C at 760 mmHg
• Flash Point: 339.7 °C
• Appearance: White powder
• Density: 1.232 g/cm³
• Vapor Pressure: 3.72E-17mmHg at 25°C
• Refractive Index: -4 ° (C=1, 80% AcOH)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 3.70±0.10(Predicted)
• BRN: 3636375
• CAS DataBase Reference: Fmoc-L-glutamic acid 5-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-glutamic acid 5-tert-butyl ester(71989-18-9)
• EPA Substance Registry System: Fmoc-L-glutamic acid 5-tert-butyl ester(71989-18-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 71989-18-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Fmoc-L-glutamic acid 5-tert-butyl ester is used as a ligand in the synthesis of cis-substituted cyclopropane carboxylic acids via C-H activation of cyclopropane carboxamides using Pd catalyst. This application takes advantage of its ability to form stable complexes with palladium catalysts, facilitating the formation of the desired cyclopropane carboxylic acid products.
Used in Pharmaceutical Industry:
Fmoc-L-glutamic acid 5-tert-butyl ester is used as a linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives. Its role as a linker allows for the efficient conjugation of multiple small molecules to the paclitaxel backbone, potentially enhancing the drug's therapeutic effects and reducing side effects.
Used in Peptide Synthesis:
Fmoc-L-glutamic acid 5-tert-butyl ester is used as a building block in the preparation of stapled α-helical peptides and peptide C-terminal thioesters. Its incorporation into these peptide structures enables the formation of stable and functional peptide-based therapeutics, with potential applications in various diseases and conditions.

InChI:InChI=1/C24H27NO6/c1-24(2,3)31-22(28)20(12-13-21(26)27)25-23(29)30-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,26,27)/t20-/m0/s1

Upstream product

• 2419-56-9 L-glutamic acid 5-tert-butyl ester 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 56-86-0 L-glutamic acid 
• 115-11-7 isobutene 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 851713-96-7 Fmoc-Glu(t-Bu)-1,1-dimethylallyl ester 

Downstream Products

• 71989-19-0 Fmoc-Glu(O-t-Bu)-ONp 
• 113534-27-3 Fmoc-Glu(OtBu)-OTDO 
• 86061-04-3 N^α-Fmoc-Glu-(O-tBu)-OPfp 
• 126771-44-6 (S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-pentanedioic acid 5-tert-butyl ester 1-[4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl] ester 
• 143063-42-7 Fmoc-Glu(OtBu)-Thr(tBu)-Gln-Arg(Mtr)-Phe-OBzl 
• 157886-21-0 Fmoc-Glu(Ot-Bu)-Asp(Ot-Bu)-OBn 
• 157886-23-2 Fmoc-Glu(Ot-Bu)-Asp(Ot-Bu)-OMbn 
• 157886-22-1 Fmoc-Glu(Ot-Bu)-Asp(Ot-Bu)-ONbn 
• 104091-09-0 (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid 
• 160002-62-0 (S)-4-Benzylsulfanylcarbonyl-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester 
• 114119-86-7 Fmoc-Glu(OtBu)-OObt 
• 154672-63-6 Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-tert-butyl ester of L-glutamic acid 
• 920288-91-1 tert-butyl N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N1-(3-phenylpropyl)-L-α-glutaminate 

Relevant articles and documents

High-efficiency industrial production method of Fmoc-Glu (Otbu)-OH

The invention relates to the field of organic synthesis, and especially relates to the technical field of a high-efficiency industrial production method of Fmoc-Glu (Otbu)-OH. The method comprises thefollowing steps: synthesizing an intermediate [Glu(OtBu)]2Cu, and then synthesizing the target product Fmoc-Glu (Otbu)-OH. The method has the advantages of great reduction of reaction steps, and goodcontrol of the reaction process. The industrial production method of the Fmoc-Glu (Otbu)-OH can efficiently and stably produce the high-quality Fmoc-Glu (Otbu)-OH, so the purity is greater than 99.5%, and the content of a single impurity is less than 0.1%.

Mild oxidative cleavage of 9-BBN-protected amino acid derivatives

Protection of the amino acid moiety using 9-BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9-BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90% yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine. A representative set of 9-BBN-protected amino acid derivatives were efficiently deprotected using peracid reagents in excellent yields. Deprotection is orthogonal with several common protecting groups. Its tolerance of highly acid sensitive groups, such as trityl-protected amides and glycosidic linkages, is especially notable.

Synthesis of l -octaarginine through microencapsulated palladium-catalyzed allyl ester deprotection

Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.

Derivates of Polyethylene Glycol Modified Thymosin Alpha 1

Pharmaceutical compositions that include thymosin alpha 1 peptide derivatives modified at the C-terminal of the peptide chain with polyethylene glycol, and their pharmaceutical acceptable salts, are generally disclosed. Also, new methods used to prepare these thymosin alpha 1 peptide derivatives modified at the C-terminal of the peptide chain with polyethylene glycol are generally provided. The presently disclosed compounds and their salts can be prepared administered to humans to treat immune disease and can also be used in adjuvant treatment.

Efficient procedure for the preparation of oligomer-free N-fmoc amino acids

A two-step method is presented for the peptide-free, high-purity, and high-yield synthesis of N-Fmoc amino acids. The first step involves the preparation of stable dicyclohexylammonium-amino acid ionic adduct in acetone. Subsequently, the ionic adducts, on reaction with Fmoc-Nosu under mild alkaline conditions, give dipeptide-free N-Fmoc amino acids. The positive charge of the dicyclohexylammonium counterion in the ionic salt has a longer radius, moderating the nucleophilicity of the carboxylate ion of the amino acid and preventing by-products by arresting the formation of mixed anhydrides, the precursors of oligopeptide impurities.

A convenient, general synthesis of 1,1-dimethylallyl esters as protecting groups for carboxylic acids

(Chemical Equation Presented) Carboxylic acids were converted in high yield to their 1,1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to be compatible with tert-butyl, benzyl, and Fmoc protecting groups, and Fmoc deprotection could be carried out selectively in the presence of DMA esters. DMA esters were also shown to be resistant to nucleophilic attack, suggesting that they will serve as alternatives to tert-butyl esters when acidic deprotection conditions need to be avoided.

GLP-2 compounds, formulations, and uses thereof

The present invention relates to novel human glucagon-like peptide-2 (GLP-2) peptides and human glucagon-like peptide-2 derivatives which have a protracted profile of action as well as polynucleotide constructs encoding such peptides, vectors and host cells comprising and expressing the polynucleotide, pharmaceutical compositions, uses and methods of treatment.

Angiopeptin cyclopeptide compounds

The invention relates to a compound selected from those of formula (I) (SEQ ID NO:1): STR1 in which R1, R2, X1 and X2 are as defined in the description, useful as inhibitor of the proliferation component of vascular smooth muscle cells.

Synthesis of ω-tert-butyl esters of aspartic acid and glutamic acid via B,B-difluoroboroxazolidones

B,B-Difluoroboroxazolidones (DFBONs) were synthesized for the first time from salts of amino acid and BF3·Et2O, and their properties were examined. DFBONs were used in selective preparation of Glu(OBu(t)) and Asp(OBu(t)) in good yields under catalysis with BF3·Et2O and H3PO4. Amberlite XAD-2 resin was successfully employed to purify the above amino acid derivatives.