Boc-L-glutamic acid γ-9-fluorenylmethyl ester
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Boc-L-glutamic acid γ-9-fluorenylmethyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002769
CAS number
123417-18-5
Molecular Formula
C24H27NO6
Molecular Weight
425.50
Boc-L-glutamic acid γ-9-fluorenylmethyl ester
IUPAC Name
(2S)-5-(9H-fluoren-9-ylmethoxy)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
Synonyms
Boc-L-Glu(OFm)-OH; Boc-L-glutamic acid 5-(9-fluorenylmethyl) ester; (S)-5-((9H-Fluoren-9-yl)methoxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid; N-alpha-tert-Butyloxycarbonylglutamic acid gamma-fluorenylmethyl ester
Appearance
White to off white powder
Purity
≥ 98% (HPLC)
Density
1.232±0.06 g/cm3(Predicted)
Melting Point
92-131 °C
Boiling Point
633.5±55.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/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
InChI Key
RCQRXYWDDVULAP-FQEVSTJZSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O

Boc-L-glutamic acid γ-9-fluorenylmethyl ester, a chemical compound utilized in peptide synthesis for its protective ester group, finds diverse applications in the field.

Peptide Synthesis: Central to solid-phase peptide synthesis (SPPS), Boc-L-glutamic acid γ-9-fluorenylmethyl ester stands as a pivotal building block. Its Fmoc protective group enables selective deprotection during peptide assembly, facilitating the synthesis of intricate peptides with precision. Researchers harness this compound to craft bespoke peptides for cutting-edge pharmaceutical studies and therapeutic advancements.

Protein Engineering: Within the realm of protein engineering, Boc-L-glutamic acid γ-9-fluorenylmethyl ester plays a vital role in introducing tailored modifications to protein architectures. By integrating this derivative into polypeptides, scientists explore protein folding dynamics, stability, and functionality. Such alterations are essential for designing proteins with refined or innovative functions.

Biomedical Research: This compound serves as a valuable tool in investigating enzyme-substrate interactions and conducting protein-ligand binding assays. Researchers leverage Boc-L-glutamic acid γ-9-fluorenylmethyl ester to engineer modified substrates that mirror natural enzyme targets. These studies yield insights into enzyme kinetics and aid in developing potent enzyme inhibitors for therapeutic interventions.

1.Synthesis of beta- and gamma-fluorenylmethyl esters of respectively N alpha-Boc-L-aspartic acid and N alpha-Boc-L-glutamic acid.
al-Obeidi F1, Sanderson DG, Hruby VJ. Int J Pept Protein Res. 1990 Mar;35(3):215-8.
The orthogonal synthesis of N alpha-Boc-L-aspartic acid-gamma-fluorenylmethyl ester and N alpha-Boc-L-glutamic acid-delta-fluorenylmethyl ester is reported. This is a four-step synthesis that relies on the selective esterification of the side-chain carboxyl groups on N alpha-CBZ-L-aspartic acid and N alpha-CBZ-L-glutamic acid. Such selectivity is accomplished by initially protecting the alpha-carboxyl group through the formation of the corresponding 5-oxo-4-oxazolidinone ring. Following side-chain esterification, the alpha-carboxyl and alpha-amino groups are deprotected with acidolysis. Finally, the alpha-amino group is reprotected with the t-butyl-oxycarbonyl (Boc) group. Thus aspartic acid and glutamic acid have their side-chain carboxyl groups protected with the base-labile fluorenylmethyl ester (OFm) and their alpha-amino groups protected with the acid-labile Boc group. These residues, when used in conjunction with N alpha-Boc-N epsilon-Fmoc-L-lysine, are important in the formation of side-chain to side-chain cyclizations, via an amide bridge, during solid-phase peptide synthesis.
2.An approach to trapping gamma-glutamyl radical intermediates proposed for vitamin K dependent carboxylase: alpha,beta-methyleneglutamic acid.
Slama JT1, Satsangi RK, Simmons A, Lynch V, Bolger RE, Suttie J. J Med Chem. 1990 Feb;33(2):824-32.
The vitamin K dependent carboxylase activates the glutamyl gamma-CH of substrate peptides for carboxylation by producing a gamma-glutamyl free radical, a gamma-glutamyl carbanion, or through a concerted carboxylation. We propose to intercept the putative gamma-glutamyl free radical by the intramolecular rearrangement of a substrate containing the alpha,beta-cyclopropane analogue of glutamic acid. The rearrangement of cyclopropylcarbinyl radicals into 2-butenyl radicals is rapid, exothermic, and considered diagnostic of free-radical formation. 1-Amino-2-(carboxymethyl)cyclopropane-1-carboxylate, the beta-cyclopropane analogue of glutamic acid, was synthesized starting from diethyl alpha-ketoglutarate. The alpha-keto ester was first treated with benzonitrile in sulfuric acid, to yield diethyl alpha,alpha-dibenzamidoglutarate. The alpha,alpha-dibenzamido acid was cleaved to produce the alpha,beta-dehydroamino acid and benzamide on treatment with p-toluenesulfonic acid in hot benzene.
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