Fmoc-L-glutamic acid γ-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino] benzyl ester
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Fmoc-L-glutamic acid γ-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino] benzyl ester

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The ODmab group is an excellent protecting group for carboxylic acids. It is orthogonal to both acid.

Category
Fmoc-Amino Acids
Catalog number
BAT-003755
CAS number
268730-86-5
Molecular Formula
C40H44N2O8
Molecular Weight
680.80
Fmoc-L-glutamic acid γ-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino] benzyl ester
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[[4-[[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-3-methylbutylidene]amino]phenyl]methoxy]-5-oxopentanoic acid
Synonyms
Fmoc-L-Glu(ODmab)-OH; (2S)-5-[[4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]phenyl]methoxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid
Appearance
White to pale yellow powder
Purity
≥ 99% (HPLC)
Density
1.251 g/cm3
Melting Point
167-172 °C
Boiling Point
851.2±65.0 °C
Storage
Store at -20 °C
InChI
InChI=1S/C40H44N2O8/c1-24(2)19-33(37-34(43)20-40(3,4)21-35(37)44)41-26-15-13-25(14-16-26)22-49-36(45)18-17-32(38(46)47)42-39(48)50-23-31-29-11-7-5-9-27(29)28-10-6-8-12-30(28)31/h5-16,24,31-32,41H,17-23H2,1-4H3,(H,42,48)(H,46,47)/t32-/m0/s1
InChI Key
DABQNXPVTHIRRK-YTTGMZPUSA-N
Canonical SMILES
CC(C)CC(=C1C(=O)CC(CC1=O)(C)C)NC2=CC=C(C=C2)COC(=O)CCC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Fmoc-L-glutamic acid γ-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino] benzyl ester is a specialized compound used primarily in peptide synthesis.

Peptide Synthesis: This compound serves as a crucial building block in the solid-phase synthesis of peptides. It provides a protected glutamic acid residue that ensures the stability of the amino acid sequence during synthesis. Its integration into peptide chains allows chemists to create complex bioactive peptides for research and therapeutic applications.

Protein Engineering: It is employed in protein engineering where modified peptides and proteins are synthesized for studying protein functions and interactions. By incorporating it into specific protein regions, researchers can introduce functional groups that modulate protein activity. This aids in designing proteins with enhanced or novel functionalities for various biomedical applications.

Drug Development: In the pharmaceutical industry, this molecule is utilized to create peptide-based drug candidates. Its structural features allow for the introduction of specific side chains that can enhance the drug’s potency, selectivity, and stability. This approach is vital for developing peptide drugs targeting diseases like cancer and autoimmune disorders.

Bioconjugation: Fmoc-L-glutamic acid γ-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino] benzyl ester can be used in bioconjugation strategies to link peptides to other biomolecules or surfaces. This enables the creation of multifunctional bioconjugates for applications such as targeted drug delivery and the development of biosensors. Its versatility in conjugation reactions expands the potential for innovative biotechnological solutions.

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