209252-17-5

Basic information

• Product Name: Fmoc-L-beta-glutamic acid 5-tert-butyl ester
• Synonyms: N-BETA-(9-FLUORENYLMETHOXYCARBONYL)-L-BETA-HOMOASPARTIC ACID GAMMA-T-BUTYL ESTER;(R)-N-BETA-(9-FLUORENYLMETHOXYCARBONYL)-3-AMINO-5-T-BUTYL ESTER-5-OXOPENTANOIC ACID;FMOC-L-BETA-GLUTAMIC ACID 5-TERT-BUTYL ESTER;FMOC-L-BETA-HOMOASPARTIC ACID 5-TERT-BUTYL ESTER;FMOC-L-BETA-HOMOASPARTIC ACID GAMMA-T-BUTYL ESTER;FMOC-L-BETA-HOMOASPARTIC ACID(OTBU);FMOC-BETA-GLU(OTBU)-OH;FMOC-BETA-HOMOASPARTIC ACID(OTBU)
• CAS NO: 209252-17-5
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.47
• Product Categories: β-Homo Amino Acids;Beta amino acids;Unusual Amino Acids;Amino Acid Derivatives
• Mol File: 209252-17-5.mol

Chemical Properties

• Melting Point: 82-83 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Boiling Point: 637 °C at 760 mmHg
• Flash Point: 339.1 °C
• Appearance: /
• Density: 1.232 g/cm³
• Vapor Pressure: 4.22E-17mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: 2-8°C
• PKA: 4.24±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 7952342
• CAS DataBase Reference: Fmoc-L-beta-glutamic acid 5-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-beta-glutamic acid 5-tert-butyl ester(209252-17-5)
• EPA Substance Registry System: Fmoc-L-beta-glutamic acid 5-tert-butyl ester(209252-17-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 209252-17-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-L-beta-glutamic acid 5-tert-butyl ester is used as a protected building block for the introduction of glutamic acid into peptides. This is important because glutamic acid is a key component in the structure and function of various peptides and proteins, which are vital for numerous biological processes and therapeutic applications.
Used in Peptide Synthesis:
Fmoc-L-beta-glutamic acid 5-tert-butyl ester is used as a key component in peptide synthesis, allowing for the efficient and controlled incorporation of glutamic acid into peptide sequences. This is crucial for the development of new drugs and therapeutic agents, as well as for research purposes in understanding the structure and function of peptides and proteins.
Used in Research and Development:
Fmoc-L-beta-glutamic acid 5-tert-butyl ester is used as a research tool for studying the role of glutamic acid in various biological processes. By incorporating this protected building block into peptide sequences, researchers can gain insights into the structure, function, and interactions of peptides and proteins, which can lead to the development of new therapeutic strategies and a better understanding of biological systems.

InChI:InChI=1/C24H27NO6/c1-24(2,3)31-22(28)13-15(12-21(26)27)25-23(29)30-14-20-18-10-6-4-8-16(18)17-9-5-7-11-19(17)20/h4-11,15,20H,12-14H2,1-3H3,(H,25,29)(H,26,27)/t15-/m1/s1

Upstream product

• 71989-14-5 Fmoc-(tBu)Asp-OH 
• 244031-63-8 tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-diazo-4-oxopentanoate 

Downstream Products

• 606149-27-3 C₃₂H₃₅N₃O₆ 
• 606149-29-5 C₃₁H₃₁N₃O₆ 
• 1026333-79-8 3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(3-p-tolyl-[1,2,4]oxadiazol-5-yl)-butyric acid allyl ester 
• 606149-34-2 (1,1-dimethylethyl-3-(R)-[[9H-fluoren-9-ylmethoxy)carbonyl]-amino]-4-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]butanoate 

Relevant articles and documents

CANCER IMAGING AND TREATMENT

A compound, or a pharmaceutically acceptable salt or ester thereof, comprises the structure: [in-line-formulae][(P1-S1j)p-L-(S2q-P2)r]t [/in-line-formulae] wherein: P1 and P2, which may be the same or

Design, synthesis, and functionalization of dimeric peptides targeting chemokine receptor CXCR4

The chemokine receptor CXCR4 is a critical regulator of inflammation and immune surveillance, and it is specifically implicated in cancer metastasis and HIV-1 infection. On the basis of the observation that several of the known antagonists remarkably shar

Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes

An efficient and stereospecific homologation of urethane-protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of Fmoc-/Boc-/Z-α-amino acid and 9-fluorenylmethyl chloroformate for the acylation of diazomethane synth

Synthesis of Fmoc-/Boc-/Z-β-amino acids via Arndt-Eistert homologation of Fmoc-/Boc-/Z-α-amino acids employing BOP and PyBOP

A simple and efficient protocol for Arndt-Eistert chain homologation of Fmoc-/Boc-/Z-α-amino acids using BOP or PyBOP as a coupling agent to the corresponding β-amino acids, synthesizing the key intermediate α-diazoketones as crystalline solids in good yield is described.

Synthesis of β-amino acids: 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (TBTU) for activation of Fmoc-/Boc-/Z-α-amino acids

A new and efficient method for the homologation of urethane protected α-amino acids to its β-homomers by the Arndt-Eistert method using TBTU as a coupling agent is described. Several Fmoc-/Boc-/Z-protected α-amino diazoketone derivatives have been obtaine

Synthesis of (R) and (S) enantiomers of Fmoc-protected 1,2,4-oxadiazole-containing β3-amino acids from Fmoc-(R)-β-HAsp(OtBu)-OH

Fmoc-(R)-β-HomoAsp(OtBu)-OH was used for the synthesis of both (R) and (S) enantiomers of various Fmoc-protected 3-substituted 1,2,4-oxadiazole-containing β3-amino acids. The 1,2,4-oxadiazole heterocycle was formed using sodium acetate, a Fmoc-

Homologation of α-amino acids to β-amino acids using Boc2O

The use of Boc2O as a coupling agent in the homologation of N-urethane protected-α-amino acid to its β-homomers by the Arndt-Eistert method is described. The homologation gives good yields without racemization. The use of Boc2O as a

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.

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.