Fmoc-L-glutamic acid γ-N-hydroxysuccinimide ester α-tert-butyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Fmoc-L-glutamic acid γ-N-hydroxysuccinimide ester α-tert-butyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
Fmoc-Amino Acids
Catalog number
BAT-003760
CAS number
200616-38-2
Molecular Formula
C28H30N2O8
Molecular Weight
522.55
Fmoc-L-glutamic acid γ-N-hydroxysuccinimide ester α-tert-butyl ester
IUPAC Name
1-O-tert-butyl 5-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioate
Synonyms
Fmoc-L-Glu(OSu)-OtBu; 1-tert-butyl 2,5-dioxopyrrolidin-1-yl 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pentanedioate; Fmoc-Glu(OSu)-OtBu; 1-O-tert-butyl 5-O-(2,5-dioxopyrrolidin-1-yl) 2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioate; 1-tert-butyl 2,5-dioxopyrrolidin-1-yl 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pentanedioate
Appearance
White to off-white powder
Purity
≥ 97% (Assay)
Storage
Store at -20 °C
InChI
InChI=1S/C28H30N2O8/c1-28(2,3)37-26(34)22(12-15-25(33)38-30-23(31)13-14-24(30)32)29-27(35)36-16-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-11,21-22H,12-16H2,1-3H3,(H,29,35)/t22-/m0/s1
InChI Key
TWIOCLGOABQUJM-QFIPXVFZSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CCC(=O)ON1C(=O)CCC1=O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-L-glutamic acid γ-N-hydroxysuccinimide ester α-tert-butyl ester, a versatile compound crucial in peptide synthesis and bioconjugation, finds diverse applications.

Peptide Synthesis: At the core of solid-phase peptide synthesis (SPPS), this compound serves as a foundational building block. Its Fmoc protection group allows for meticulous deprotection and coupling reactions, facilitating the synthesis of intricate peptides. Researchers harness this reagent to integrate glutamic acid residues into peptide chains, ensuring exceptional purity and yield.

Protein Engineering: In the domain of protein engineering, Fmoc-L-glutamic acid γ-N-hydroxysuccinimide ester α-tert-butyl ester is a vital tool for introducing precise modifications at glutamic acid sites within proteins. This alteration can reshape the protein’s structure and function, enabling the creation of proteins with enhanced properties. It stands as an indispensable instrument for crafting proteins with novel therapeutic and industrial applications.

Bioconjugation: Integral to bioconjugation techniques, this compound acts as a linchpin in linking bioactive molecules to proteins, antibodies, or nanoparticles. Its reactive ester group facilitates the formation of stable amide bonds with primary amines, enabling the synthesis of versatile bioconjugates. This intricate process lies at the heart of developing advanced drug delivery systems and diagnostic tools.

Drug Discovery: In the realm of drug discovery, Fmoc-L-glutamic acid γ-N-hydroxysuccinimide ester α-tert-butyl ester assumes a pivotal role in synthesizing peptide-based drugs. Its application allows for the precise incorporation of glutamic acid analogs that can enhance drug stability and efficacy. Researchers leverage this compound to innovate and optimize potential therapeutic peptides, advancing the frontier of drug development.

1. Amino acid-azetidine chimeras: synthesis of enantiopure 3-substituted azetidine-2-carboxylic acids
Z Sajjadi, W D Lubell J Pept Res. 2005 Feb;65(2):298-310. doi: 10.1111/j.1399-3011.2005.00228.x.
Azetidine-2-carboxylic acid (Aze) analogs possessing various heteroatomic side chains at the 3-position have been synthesized by modification of 1-9-(9-phenylfluorenyl) (PhF)-3-allyl-Aze tert-butyl ester (2S,3S)-1. 3-Allyl-Aze 1 was synthesized by regioselective allylation of alpha-tert-butyl beta-methyl N-(PhF)aspartate 13, followed by selective omega-carboxylate reduction, tosylation, and intramolecular N-alkylation. Removal of the PhF group and olefin reduction by hydrogenation followed by Fmoc protection produced nor-leucine-Aze chimera 2. Regioselective olefin hydroboration of (2S,3S)-1 produced primary alcohol 23, which was protected as a silyl ether, hydrogenated and N-protected to give 1-Fmoc-3-hydroxypropyl-Aze 26. Enantiopure (2S,3S)-3-(3-azidopropyl)-1-Fmoc-azetidine-2-carboxylic acid tert-butyl ester 3 was prepared as a Lys-Aze chimera by activation of 3-hydroxypropyl-Aze 26 as a methanesulfonate and displacement with sodium azide. Moreover, orthogonally protected azetidine dicarboxylic acid 4 was synthesized as an alpha-aminoadipate-Aze chimera by oxidation of alcohol 26. These orthogonally protected amino acid-Aze chimeras are designed to serve as tools for studying the influence of conformation on peptide activity.
2. A novel [60]fullerene amino acid for use in solid-phase peptide synthesis
F Pellarini, D Pantarotto, T Da Ros, A Giangaspero, A Tossi, M Prato Org Lett. 2001 Jun 14;3(12):1845-8. doi: 10.1021/ol015934m.
[see structure]. A fullerene derivative containing a free amino group has been condensed with N-Fmoc-L-glutamic acid alpha-tert-butyl ester to give a C60-functionalized amino acid. The carboxylic end of this amino acid has been deprotected in acidic conditions, and the resulting acid has been used for solid-phase peptide synthesis. The final peptide, cleaved from the resin, was very soluble in water solutions and showed antimicrobial activity against two representative bacteria.
3. Quinazoline antifolate thymidylate synthase inhibitors: gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583)
V Bavetsias, A L Jackman, R Kimbell, W Gibson, F T Boyle, G M Bisset J Med Chem. 1996 Jan 5;39(1):73-85. doi: 10.1021/jm950471+.
The syntheses of gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583) are described. The general methodology for the synthesis of these molecules involved the preparation of the dipeptide derivatives employing solution phase peptide synthesis followed by condensation of the dipeptide free bases with the appropriate pteroic acid analogue via diethyl cyanophosphoridate (DEPC) activation. In the final step, tert-butyl esters were removed by trifluoroacetic acid (TFA) hydrolysis. Z-L-Glu-OBut-gamma-D-Ala-OBut, for example, was prepared from alpha-tert-butyl N-(benzyloxycarbonyl)-L-glutamate and tert-butyl D-alaninate via isobutyl-mixed anhydride coupling. The Z-group was removed by catalytic hydrogenolysis and the resulting dipeptide free base condensed with 2-desamino-2-methyl-N10-propargyl-5,8-dideazapteroic acid via DEPC coupling. Finally, tert-butyl esters were removed by TFA hydrolysis to give ICI 198583-gamma-D-Ala. The compounds were tested as inhibitors of thymidylate synthase and L1210 cell growth. Good enzyme and growth inhibitory activity were found with gamma-linked L-D dipeptides, the best examples being the Glu-gamma-D-Glu derivative 35 (Ki = 0.19 nM, L1210 IC50 = 0.20 +/- 0.017 microM) and the Glu-gamma-D-alpha-aminoadipate derivative 39 (Ki = 0.12 nM, L1210 IC50 = 0.13 +/- 0.063 microM). In addition, ICI 198583 L-gamma-D-linked dipeptides were resistant to enzymatic degradation in mice.
Online Inquiry
Inquiry Basket