N-α-(9-Fluorenylmethoxycarbonyl)-N-β-(4,4'-dimethoxybenzhydryl)-L-asparagine
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N-α-(9-Fluorenylmethoxycarbonyl)-N-β-(4,4'-dimethoxybenzhydryl)-L-asparagine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005451
CAS number
113534-16-0
Molecular Formula
C34H32N2O7
Molecular Weight
580.64
N-α-(9-Fluorenylmethoxycarbonyl)-N-β-(4,4'-dimethoxybenzhydryl)-L-asparagine
IUPAC Name
(2S)-4-[bis(4-methoxyphenyl)methylamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
Synonyms
Fmoc-Asn(Mbh)-OH; Fmoc-Asn(Dod)-OH; (2S)-4-[bis(4-methoxyphenyl)methylamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid; N-Fmoc-L-Asparagine (DOD); Nalpha-Fmoc-Nalpha-(4,4 inverted exclamation marka-dimethoxybenzhydryl)-L-asparagine; Nalpha-Fmoc-Ngamma-(4,4'-dimethoxybenzhydryl)-L-asparagine
Purity
≥ 95%
Density
1.278 g/cm3
Boiling Point
857.5 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C34H32N2O7/c1-41-23-15-11-21(12-16-23)32(22-13-17-24(42-2)18-14-22)36-31(37)19-30(33(38)39)35-34(40)43-20-29-27-9-5-3-7-25(27)26-8-4-6-10-28(26)29/h3-18,29-30,32H,19-20H2,1-2H3,(H,35,40)(H,36,37)(H,38,39)/t30-/m0/s1
InChI Key
NUINEVHFMAGARJ-PMERELPUSA-N
Canonical SMILES
COC1=CC=C(C=C1)C(C2=CC=C(C=C2)OC)NC(=O)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

N-α-(9-Fluorenylmethoxycarbonyl)-N-β-(4,4’-dimethoxybenzhydryl)-L-asparagine, often abbreviated as Fmoc-Dmb-Asn, is a synthetic amino acid derivative used primarily in peptide synthesis. Here are some key applications of Fmoc-Dmb-Asn:

Peptide Synthesis: Fmoc-Dmb-Asn is widely used in solid-phase peptide synthesis (SPPS) to incorporate asparagine residues into peptides. The Fmoc and Dmb protecting groups are essential for maintaining the asparagine’s integrity during the synthesis process. This derivative allows for the efficient and high-purity production of peptides with asparagine residues without side reactions.

Protein Engineering: In protein engineering, Fmoc-Dmb-Asn is used to create modified peptides that are incorporated into larger protein structures. By strategically placing Fmoc-Dmb-Asn within a peptide sequence, researchers can introduce specific asparagine residues necessary for protein function or stability. This application is vital for studying protein-protein interactions and designing novel proteins with enhanced properties.

Drug Development: Fmoc-Dmb-Asn is utilized in the synthesis of peptide-based drug candidates. The incorporation of protected asparagine into bioactive peptides allows for the generation of therapeutic compounds with desired pharmacokinetic and pharmacodynamic properties. These peptides can be crucial for targeting diseases such as cancer, metabolic disorders, and infectious diseases.

Bioconjugation: In bioconjugation, Fmoc-Dmb-Asn serves as a building block for attaching peptides to various biomolecules, such as antibodies or nanoparticles. The presence of protected asparagine residues enables site-specific conjugation, ensuring that the functional groups remain accessible for subsequent binding or activity. This precise attachment is essential for developing targeted drug delivery systems and diagnostic tools.

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