N-α-(9-Fluorenylmethoxycarbonyl)-L-glutamic acid γ-t-butyl ester
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N-α-(9-Fluorenylmethoxycarbonyl)-L-glutamic acid γ-t-butyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-005437
CAS number
71989-18-9
Molecular Formula
C24H27NO6
Molecular Weight
425.47
N-α-(9-Fluorenylmethoxycarbonyl)-L-glutamic acid γ-t-butyl ester
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
Synonyms
Fmoc-Glu(OtBu)-OH,Nonhydrate; Fmoc-Glu(OtBu)-OH Hydrate; Fmoc-L-glutamic acid 5-tert-butyl ester; Fmoc-L-Glu(OtBu)-OH hydrate; Fmoc-L-glutamic acid 5-tert-butyl ester hydrate; Fmoc-L-glutamic acid γ-tert-butyl ester hydrate
Appearance
White powder
Purity
≥ 99.7% (Chiral HPLC)
Density
1.232±0.060 g/cm3
Melting Point
80-100 °C
Boiling Point
633.5±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H27NO6/c1-24(2,3)31-21(26)13-12-20(22(27)28)25-23(29)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
OTKXCALUHMPIGM-FQEVSTJZSA-N
Canonical SMILES
CC(C)(C)OC(=O)CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

N-α-(9-Fluorenylmethoxycarbonyl)-L-glutamic acid γ-t-butyl ester, a chemical compound employed as a protecting group in peptide synthesis, finds diverse applications in various fields.

Peptide Synthesis: In the realm of organic chemistry, N-α-(9-Fluorenylmethoxycarbonyl)-L-glutamic acid γ-t-butyl ester serves as a pivotal component in solid-phase peptide synthesis, acting as a safeguard for the amine functionality of amino acids. This protective shield prevents undesired side reactions during peptide coupling, enabling the gradual assembly of peptides. Following synthesis, these protective groups can be selectively removed without compromising the peptide’s structure, showcasing precise control over peptide formation.

Pharmaceutical Research: Embedded within the fabric of pharmaceutical innovation, this compound plays a critical role in the creation of peptide-based therapeutics. By harnessing N-α-(9-Fluorenylmethoxycarbonyl) as a protective shield, researchers can craft intricate peptides with exceptional accuracy and purity. These synthetic peptides hold promise as potential candidates for drug development, offering a potential avenue in combating a myriad of diseases, spanning from cancer to autoimmune disorders, with pinpoint accuracy.

Biochemical Studies: N-α-(9-Fluorenylmethoxycarbonyl)-L-glutamic acid γ-t-butyl ester finds application in building peptide libraries for screening and identifying bioactive peptides. These libraries are instrumental in uncovering the interactions between peptides and biological molecules such as proteins and enzymes. By shedding light on these interactions, studies in this realm contribute significantly to unraveling biological processes and forging novel biochemical tools, underpinning further advancements in the field.

Chemical Modifications: Leveraging protective groups like N-α-(9-Fluorenylmethoxycarbonyl), researchers can carry out precise chemical conjugations, such as coupling targeting moieties or fluorescent tags at designated sites. These modifications play a pivotal role in propelling peptide-based research and therapeutic applications to new heights.

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