Fmoc-Asp(OtBu)-Opfp
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Fmoc-Asp(OtBu)-Opfp

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Category
Fluorinated Amino Acids
Catalog number
BAT-005299
CAS number
86061-01-0
Molecular Formula
C29H24NO6F5
Molecular Weight
577.50
Fmoc-Asp(OtBu)-Opfp
IUPAC Name
4-O-tert-butyl 1-O-(2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioate
Synonyms
4-O-tert-butyl 1-O-(2,3,4,5,6-pentafluorophenyl)(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioate
Appearance
White powder
Purity
≧ 95%
Density
1.373 g/cm3
Melting Point
90-100 °C
Boiling Point
666.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C29H24F5NO6/c1-29(2,3)41-20(36)12-19(27(37)40-26-24(33)22(31)21(30)23(32)25(26)34)35-28(38)39-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,35,38)/t19-/m0/s1
InChI Key
DWYWJUBBXKYAMY-IBGZPJMESA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-Asp(OtBu)-Opfp, a specialized reagent pivotal in peptide synthesis and biochemical research, finds diverse applications. Here are four key utilities of Fmoc-Asp(OtBu)-Opfp articulated with a high degree of perplexity and burstiness:

Solid-Phase Peptide Synthesis: A cornerstone of peptide synthesis, Fmoc-Asp(OtBu)-Opfp shines in solid-phase peptide synthesis (SPPS) as a protective amino acid derivative. It aids in constructing peptide chains by safeguarding amino and carboxyl groups from unwanted side reactions. The presence of the Fmoc group enables selective deprotection under gentle conditions, streamlining peptide assembly with greater efficiency and precision.

Development of Peptidomimetics: Envisioned for drug discovery, Fmoc-Asp(OtBu)-Opfp plays a pivotal role in crafting peptidomimetics - altered peptides mimicking natural counterparts in structure and function. This reagent facilitates the inclusion of aspartic acid residues with specific protective groups, amplifying the stability and bioactivity of resultant compounds. Peptidomimetics can be tailored to target distinct proteins or receptors for therapeutic pursuits.

Functionalization of Peptides: Delving into the site-specific functionalization of peptides, Fmoc-Asp(OtBu)-Opfp empowers the introduction of diverse chemical groups at designated positions within peptide sequences. This versatility enables researchers to adorn peptides with fluorescent tags, biotin, or other functional moieties for purposes ranging from detection to purification or studying biological interactions. Such functionalization underpins the development of peptide-based probes and therapies.

Enzyme Mechanism Studies: Within the realm of enzymology, Fmoc-Asp(OtBu)-Opfp emerges as a key tool for synthesizing substrate analogs or inhibitors aimed at unraveling enzyme mechanisms. Researchers leverage this reagent to craft peptides featuring modified aspartic acid residues, dissecting enzyme-substrate interactions and catalytic processes. These explorations not only illuminate enzyme function but also lay the groundwork for designing precise inhibitors tailored for therapeutic interventions.

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