Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester
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Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester

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Category
Fluorinated Amino Acids
Catalog number
BAT-004560
CAS number
86061-04-3
Molecular Formula
C30H26F5NO6
Molecular Weight
591.50
Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester
IUPAC Name
5-O-tert-butyl 1-O-(2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioate
Synonyms
Fmoc-L-Glu(OtBu)-OPfp; 5-O-tert-butyl 1-O-(2,3,4,5,6-pentafluorophenyl)(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioate
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.352±0.06 g/cm3
Melting Point
119-126 °C
Boiling Point
674.2±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C30H26F5NO6/c1-30(2,3)42-21(37)13-12-20(28(38)41-27-25(34)23(32)22(31)24(33)26(27)35)36-29(39)40-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,36,39)/t20-/m0/s1
InChI Key
AIDYQYOPUBOMTR-FQEVSTJZSA-N
Canonical SMILES
CC(C)(C)OC(=O)CCC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester is a modified derivative of L-glutamic acid, where the amino group is protected with a 9-fluorenylmethoxycarbonyl (Fmoc) group, the γ-carboxyl group is esterified with a tert-butyl group, and the α-carboxyl group is esterified with a pentafluorophenyl group. This compound is commonly used in peptide synthesis and organic chemistry due to the stability provided by the protective groups, which allow selective reactions and modifications of specific functional groups. It is particularly useful in the preparation of peptides with glutamic acid residues.

One of the key applications of Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester is in peptide synthesis. The Fmoc group serves as a protective group for the amino functionality of glutamic acid, which can be selectively deprotected under mild basic conditions, allowing for controlled peptide chain elongation. The tert-butyl and pentafluorophenyl ester groups provide further protection to the carboxyl groups of glutamic acid, ensuring that specific reactions occur only at the desired sites. This makes the compound ideal for synthesizing peptides with modified or stabilized glutamic acid residues.

Another important application of Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester is in the design of bioactive peptides for drug discovery. The compound’s modified structure allows for the incorporation of unique glutamic acid derivatives into peptide sequences, which can result in peptides with enhanced stability, selectivity, and bioactivity. These peptides may be used as potential therapeutic agents targeting specific biological pathways, such as those involved in immune modulation, enzyme inhibition, or receptor binding. This application is particularly important in pharmaceutical research, where custom-designed peptides are sought after for novel drug candidates.

Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester is also utilized in the synthesis of cyclic peptides. The stability of the protective groups and the unique chemical properties of the compound make it well-suited for the creation of cyclic peptides, which are of increasing interest in drug development. These cyclic peptides can be used in a variety of therapeutic applications, including as protein mimetics, enzyme inhibitors, or targeting ligands for specific receptors. The ability to easily introduce modifications into the peptide structure is crucial for creating peptides with desirable functional properties.

Finally, Fmoc-L-glutamic acid γ-tert-butyl ester α-pentafluorophenyl ester is applied in the development of new materials, such as polymers for drug delivery systems. The modified glutamic acid residue can be incorporated into polymer chains to improve the solubility, biocompatibility, and stability of the resulting material. These polymers can be designed to deliver therapeutic agents in a controlled manner, offering advantages in the treatment of diseases that require sustained release of drugs. This application is significant in the field of materials science and biomedical engineering.

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