123417-18-5

Basic information

• Product Name: BOC-GLU(OFM)-OH
• Synonyms: BOC-L-GLUTAMIC ACID ALPHA-9-FLUORENYLMETHYL ESTER;BOC-L-GLUTAMIC ACID GAMMA-9-FLUORENYLMETHYL ESTER;BOC-L-GLUTAMIC ACID-GAMMA-FLUORENYLMETHYL ESTER;N-ALPHA-T-BUTYLOXYCARBONYL-L-GLUTAMIC ACID-BETA-FLUORENYLMETHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID ALPHA-9-FLUORENYLMETHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID GAMMA-9-FLUORENYL METHYL ESTER;Boc-L-glutamic acid γ-9-fluorenylmethyl ester;N-alpha-t-Butyloxycarbonyl-D-Glutamicacid-beta-fluorenylmethylester
• CAS NO: 123417-18-5
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.47
• EINECS: 1533716-785-6
• Product Categories: Glutamic acid [Glu, E]
• Mol File: 123417-18-5.mol

Chemical Properties

• Melting Point: 130-131 °C
• Boiling Point: 633.5 °C at 760 mmHg
• Flash Point: 336.9 °C
• Appearance: /
• Density: 1.232 g/cm³
• Vapor Pressure: 6.39E-17mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: 2-8°C
• PKA: 3.80±0.10(Predicted)
• CAS DataBase Reference: BOC-GLU(OFM)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-GLU(OFM)-OH(123417-18-5)
• EPA Substance Registry System: BOC-GLU(OFM)-OH(123417-18-5)

Safety Data

• Hazardous Substances Data: 123417-18-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-GLU(OFM)-OH is used as a building block in the synthesis of peptides and proteins for various therapeutic applications. Its chemical properties allow for the formation of stable peptide bonds, which are essential for the structure and function of biologically active molecules.
Used in Biotechnology Industry:
BOC-GLU(OFM)-OH is used as a reagent in solid-phase peptide synthesis, a technique used to produce peptides and proteins in a stepwise manner. This method allows for the efficient and controlled synthesis of complex peptide sequences, which can be used for research, drug development, and other applications.
Used in Insulin Synthesis:
BOC-GLU(OFM)-OH is used in the synthesis of [AspB10,LysB28,ProB29]-ester insulin, a modified form of insulin with improved pharmacokinetic properties. This modified insulin has potential applications in the treatment of diabetes, as it may offer advantages over traditional insulin formulations in terms of efficacy and convenience.

InChI:InChI=1/C24H27NO6/c1-24(2,3)31-23(29)25-20(22(27)28)12-13-21(26)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,27,28)/t20-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 141215-68-1 L-glutamic acid γ-9-fluorenylmethyl ester 
• 80994-44-1 {[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile 
• 129046-85-1 L-glutamic acid δ-fluorenylmethyl ester hydrochloride 
• 56-86-0 L-glutamic acid 
• 24324-17-2 9-Fluorenylmethanol 

Relevant articles and documents

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry

(Chemical Equation Presented) A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H- fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods. 2009 American Chemical Society.

Single step syntheses of ω-9-fluorenylmethyl esters of aspartic and glutamic acids

Base lability of the 9-fluorenylmethyl ester makes this group useful in solid phase peptide synthesis when used in combination with the tBoc methodology for preparing cyclic peptides. We describe a simple one step synthesis of the 9-fluorenylmethyl esters of aspartic and glutamic acids.

Convenient Syntheses of Fluorenylmethyl-Based Side Chain Derivatives of Glutamic and Aspartic acids, Lysine and Cysteine

Efficient and practical one-pot syntheses of the fluorenylmethyl-based side chain derivatives of glutamic and aspartic acids, lysine, and cysteine are described.Likewise, stability/lability of these derivatives towards solvents and reagents used in solid