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

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Category
Fluorinated Amino Acids
Catalog number
BAT-005305
CAS number
200335-75-7
Molecular Formula
C29H24NO6F5
Molecular Weight
577.50
Fmoc-D-Asp(OtBu)-Opfp
IUPAC Name
4-O-tert-butyl 1-O-(2,3,4,5,6-pentafluorophenyl) (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioate
Synonyms
4-O-tert-butyl 1-O-(2,3,4,5,6-pentafluorophenyl)(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioate; N-[(9H-Fluoren-9-Ylmethoxy)Carbonyl]-D-Aspartic Acid 4-(1,1-Dimethylethyl)1-(Pentafluorophenyl) Ester
Purity
≥ 95%
Density
1.373 g/cm3
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-/m1/s1
InChI Key
DWYWJUBBXKYAMY-LJQANCHMSA-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-D-Asp(OtBu)-Opfp, a versatile chemical reagent, plays a crucial role in peptide synthesis and bioconjugation. Here are four key applications of Fmoc-D-Asp(OtBu)-Opfp, presented with high perplexity and burstiness:

Solid-Phase Peptide Synthesis: Employing Fmoc-D-Asp(OtBu)-Opfp in solid-phase peptide synthesis facilitates the incorporation of D-aspartic acid residues into peptide chains. The Fmoc protecting group ensures precise deprotection, while the tBu ester shields the side chain carboxyl group. This reagent enables the synthesis of peptides with intricate sequences and configurations, pivotal for biochemical and therapeutic investigations.

Protein Engineering: In the realm of protein engineering, Fmoc-D-Asp(OtBu)-Opfp shines in introducing modified aspartic acid residues into proteins. By strategically integrating this reagent, researchers can alter protein structures and functions, bolstering protein stability or activity. Such modifications are invaluable for crafting novel enzymes, therapeutic proteins, and biocatalysts, pushing the boundaries of protein engineering.

Bioconjugation: Fmoc-D-Asp(OtBu)-Opfp finds its niche in bioconjugation protocols, where it serves to link peptides or proteins to other biomolecules such as fluorophores or drugs. The OPfp ester enhances coupling reactions, ensuring exceptional yield and specificity.

Peptide-Based Drug Development: In the realm of drug development, Fmoc-D-Asp(OtBu)-Opfp emerges as a key player in synthesizing peptide-based drugs with enhanced properties. By integrating D-aspartic acid residues, researchers can elevate the metabolic stability and bioavailability of peptide therapeutics. This strategy underpins the creation of more potent and long-lasting pharmaceutical compounds, advancing the field of peptide-based drug development.

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