N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-L-alanine
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N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005510
CAS number
127273-06-7
Molecular Formula
C19H16N2O4
Molecular Weight
336.35
N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-L-alanine
IUPAC Name
(2S)-3-cyano-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-Ala(3-CN)-OH; Fmoc-Ala(β-CN)-OH; (2S)-3-cyano-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-cyanopropanoic acid; Fmoc-Asp(CN)-OH; Fmoc-(S)-2-amino-3-cyanopropanoic acid; L-2-(9-fluorenylmethoxycarbonylamino)-3-cyanopropionic acid; Fmoc-β-cyano-L-alanine; Fmoc-β-Cyano-L-Ala-OH
Appearance
White solid
Purity
≥ 95% (HPLC)
Density
1.331±0.060 g/cm3
Melting Point
106-107 °C
Boiling Point
617.1±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C19H16N2O4/c20-10-9-17(18(22)23)21-19(24)25-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9,11H2,(H,21,24)(H,22,23)/t17-/m0/s1
InChI Key
FJSOTHAUCCEZLI-KRWDZBQOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC#N)C(=O)O

N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-L-alanine (Fmoc-β-Cyano-L-alanine) finds its niche as a specialized amino acid derivative with diverse applications in biochemical and biotechnological realms. Here are the key applications of N-α-(9-Fluorenylmethoxycarbonyl)-β-cyano-L-alanine unpacked with heightened perplexity and burstiness:

Peptide Synthesis: Delving into solid-phase peptide synthesis, researchers leverage Fmoc-β-Cyano-L-alanine to infuse peptides with distinct side chains and functional groups, ushering in novel properties and functionalities. This innovative approach allows for the tailored design of peptides tailored for applications in drug discovery and therapeutic interventions.

Protein Engineering: With its foray into protein engineering, Fmoc-β-Cyano-L-alanine seamlessly integrates into proteins to explore the impacts of specific side-chain alterations on protein structure and function. This exploration illuminates the nuances of protein folding, stability, and interactions, paving the way for the creation of proteins with enhanced or entirely new functionalities destined for industrial and medical utilization.

Enzyme Mechanism Studies: At the frontier of enzymology, Fmoc-β-Cyano-L-alanine takes center stage in unraveling enzyme mechanisms. By intricately inserting this modified amino acid into enzyme active sites, researchers delve into enzyme-substrate dynamics and catalytic pathways. This profound insight into enzyme function not only enriches our understanding but also catalyzes the development of enzyme modulators.

Chemical Biology: Entering the realm of chemical biology, Fmoc-β-Cyano-L-alanine emerges as a pivotal tool for interrogating post-translational modifications and protein interactions. Enabling the synthesis of peptides and proteins adorned with specific chemical alterations akin to natural modifications, this methodology aids in deciphering the roles of modifications in cellular processes and pathological conditions.

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