N-α-(9-Fluorenylmethoxycarbonyl)-D-alaninal
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N-α-(9-Fluorenylmethoxycarbonyl)-D-alaninal

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Category
Fmoc-Amino Acids
Catalog number
BAT-005424
CAS number
127043-32-7
Molecular Formula
C18H17NO3
Molecular Weight
295.33
N-α-(9-Fluorenylmethoxycarbonyl)-D-alaninal
IUPAC Name
9H-fluoren-9-ylmethyl N-[(2R)-1-oxopropan-2-yl]carbamate
Synonyms
Fmoc-D-Ala-CHO; Fmoc-D-Ala-aldehyde
Purity
≥ 95%
InChI
InChI=1S/C18H17NO3/c1-12(10-20)19-18(21)22-11-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-10,12,17H,11H2,1H3,(H,19,21)/t12-/m1/s1
InChI Key
LJGFXAKKZLFEDR-GFCCVEGCSA-N
Canonical SMILES
CC(C=O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

N-α-(9-Fluorenylmethoxycarbonyl)-D-alaninal, also known as Fmoc-D-alaninal, is a protected form of the amino acid D-alanine used in peptide synthesis and biochemical studies. Here are some key applications of N-α-(9-Fluorenylmethoxycarbonyl)-D-alaninal:

Peptide Synthesis: Fmoc-D-alaninal is commonly used in solid-phase peptide synthesis as a building block for creating peptides and proteins. The Fmoc group provides temporary protection to the amino group, allowing for sequential addition of amino acids. This results in the creation of high-purity peptides for use in research and drug development.

Protease Inhibition Studies: Fmoc-D-alaninal serves as an inhibitor in protease activity assays, helping researchers study enzyme kinetics and mechanisms. By inhibiting protease enzymes, the compound allows scientists to investigate enzyme specificity and function. This can lead to the development of new inhibitors for therapeutic applications.

Chiral Resolution: The use of Fmoc-D-alaninal in chiral resolution methods enables the separation of enantiomers in complex mixtures. Its chiral nature makes it a valuable tool for distinguishing between different stereoisomers of amino acids and peptides. This application is critical in the production of pharmaceuticals, where the chirality of a molecule can impact its biological activity.

Structural Biology: Fmoc-D-alaninal is used in structural biology to study protein folding and stability. By incorporating D-alanine derivatives into peptide sequences, researchers can examine the effects on the three-dimensional structure of proteins. This insight is important for understanding protein function and for designing stable protein-based therapeutics.

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