L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 5-(phenylmethyl)ester


Chemical Name: L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 5-(phenylmethyl)ester
CAS Number: 123639-61-2
Product Number: AG00HHDM(AGN-PC-0PHN13)
Synonyms:
MDL No:
Molecular Formula: C27H25NO6
Molecular Weight: 459.4905

Identification/Properties


Computed Properties
Molecular Weight:
459.498g/mol
XLogP3:
4.4
Hydrogen Bond Donor Count:
2
Hydrogen Bond Acceptor Count:
6
Rotatable Bond Count:
11
Exact Mass:
459.168g/mol
Monoisotopic Mass:
459.168g/mol
Topological Polar Surface Area:
102A^2
Heavy Atom Count:
34
Formal Charge:
0
Complexity:
683
Isotope Atom Count:
0
Defined Atom Stereocenter Count:
1
Undefined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Covalently-Bonded Unit Count:
1
Compound Is Canonicalized:
Yes

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Chemical Structure



Fmoc-Glu(OBzl)-OH is a key compound used in chemical synthesis for the solid-phase peptide synthesis (SPPS) of peptides. This building block, which consists of a protected glutamic acid residue with Fmoc (9-fluorenylmethyloxycarbonyl) on the α-amine and benzyl (Bzl) protection on the side chain carboxyl group, serves as a valuable tool in the construction of peptide sequences.One crucial application of Fmoc-Glu(OBzl)-OH is its utility as a coupling reagent during the assembly of peptides on a solid support. By selectively deprotecting and activating the Fmoc group for amino acid coupling, it enables the stepwise elongation of peptide chains with high efficiency and fidelity. Additionally, the benzyl ester protection on the glutamic acid side chain ensures the stability of the amino acid residue during the synthesis, allowing for the controlled manipulation of peptide structure.Moreover, the strategic use of Fmoc-Glu(OBzl)-OH in SPPS offers chemists the flexibility to introduce glutamic acid functionalities at specific positions within the peptide sequence. This enables the incorporation of acidic amino acids with precise control over the sequence diversity and properties of the synthesized peptides.Overall, Fmoc-Glu(OBzl)-OH plays a crucial role in the synthesis of complex peptides with tailored structures and functionalities, making it an indispensable tool in peptide chemistry and drug discovery research.