Cas no 103321-50-2 (Fmoc-l-alanyl Chloride)

Fmoc-L-alanyl chloride is a protected amino acid derivative widely used in peptide synthesis. The Fmoc (9-fluorenylmethoxycarbonyl) group serves as a temporary protecting group for the amine functionality, enabling selective deprotection under mild basic conditions. This reagent is particularly valuable in solid-phase peptide synthesis (SPPS) due to its high reactivity with nucleophiles, facilitating efficient coupling with amino acids or peptide chains. Its stability under typical SPPS conditions ensures reliable performance in automated synthesis. The chloride leaving group enhances acylation efficiency, reducing side reactions. Fmoc-L-alanyl chloride is preferred for its compatibility with orthogonal protection strategies and its role in producing high-purity peptides for research and pharmaceutical applications.
Fmoc-l-alanyl Chloride structure
Fmoc-l-alanyl Chloride structure
Product Name:Fmoc-l-alanyl Chloride
CAS No:103321-50-2
MF:C18H16ClNO3
MW:329.777544021606
MDL:MFCD00235802
CID:125591
PubChem ID:11142085
Update Time:2025-06-25

Fmoc-l-alanyl Chloride Chemical and Physical Properties

Names and Identifiers

    • FMOC-ALA-CL
    • Fmoc-L-Ala-Cl
    • Fmoc-L-alanyl chloride
    • (1-chlorocarbonylethyl)carbamic acid 9H-fluoren-9-ylmethyl ester
    • Fmoc-alanine acid chloride
    • Fmoc-alanine chloride
    • L-Fmoc-alanine chloride
    • Fmoc-L-Phe-Cl
    • Fmoc-Beta -Ala-Cl
    • NALPHA-9-fluorenylmethoxycarbonyl-L-alanyl chloride
    • (S)-(9H-Fluoren-9-yl)methyl(1-chloro-1-oxopropan-2-yl)carbamate
    • N-[(1S)-1-(Chlorocarbonyl)ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester
    • SCHEMBL732417
    • (9H-fluoren-9-yl)methyl (S)-(1-chloro-1-oxopropan-2-yl)carbamate
    • J-000932
    • DTXSID20456762
    • AFMYCMGTXVCJCH-NSHDSACASA-N
    • 9h-fluoren-9-ylmethyl ((2s)-1-chloro-1-oxo-2-propanyl)carbamate
    • A851179
    • I10426
    • 103321-50-2
    • MFCD00235802
    • (S)-(9H-fluoren-9-yl)methyl 1-chloro-1-oxopropan-2-ylcarbamate
    • (S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)amino]-propionyl chloride
    • 9H-FLUOREN-9-YLMETHYL N-[(2S)-1-CHLORO-1-OXOPROPAN-2-YL]CARBAMATE
    • (9H-fluoren-9-yl)methyl(S)-(1-chloro-1-oxopropan-2-yl)carbamate
    • AKOS015913830
    • Fmoc-l-alanyl Chloride
    • MDL: MFCD00235802
    • Inchi: 1S/C18H16ClNO3/c1-11(17(19)21)20-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,20,22)/t11-/m0/s1
    • InChI Key: AFMYCMGTXVCJCH-NSHDSACASA-N
    • SMILES: ClC([C@H](C)NC(=O)OCC1C2C=CC=CC=2C2C=CC=CC1=2)=O

Computed Properties

  • Exact Mass: 329.08200
  • Monoisotopic Mass: 329.0818711g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 6
  • Complexity: 434
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4
  • Topological Polar Surface Area: 55.4?2

Experimental Properties

  • Density: 1.285±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 108-110 oC
  • Solubility: Almost insoluble (0.011 g/l) (25 o C),
  • PSA: 55.40000
  • LogP: 4.06990

Fmoc-l-alanyl Chloride Pricemore >>

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Fmoc-l-alanyl Chloride Production Method

Fmoc-l-alanyl Chloride Related Literature

Additional information on Fmoc-l-alanyl Chloride

Recent Advances in Fmoc-l-alanyl Chloride (CAS: 103321-50-2) and Its Applications in Chemical Biology and Pharmaceutical Research

Fmoc-l-alanyl Chloride (CAS: 103321-50-2) is a critical reagent in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS) methodologies. This compound, which features a fluorenylmethyloxycarbonyl (Fmoc) protecting group, is widely utilized for the introduction of alanine residues into peptide chains. Recent studies have highlighted its importance in the development of novel therapeutic peptides, peptidomimetics, and bioconjugates, underscoring its versatility in chemical biology and pharmaceutical research.

One of the most significant advancements in the use of Fmoc-l-alanyl Chloride is its role in the synthesis of peptide-based drugs. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy in the rapid and efficient coupling of alanine residues, enabling the production of high-purity peptides with minimal side reactions. The study also emphasized the compound's stability under standard SPPS conditions, making it a preferred choice for industrial-scale peptide manufacturing.

In addition to its applications in peptide synthesis, Fmoc-l-alanyl Chloride has been explored for its potential in drug delivery systems. Research published in Bioconjugate Chemistry in early 2024 revealed that Fmoc-l-alanyl Chloride could be used to modify nanoparticles for targeted drug delivery. The study reported that the Fmoc group facilitated the attachment of therapeutic peptides to nanoparticle surfaces, enhancing their bioavailability and specificity. This innovation opens new avenues for the treatment of diseases such as cancer and neurodegenerative disorders.

Another area of interest is the use of Fmoc-l-alanyl Chloride in the development of antimicrobial peptides (AMPs). A recent study in ACS Infectious Diseases highlighted its role in synthesizing AMPs with enhanced stability and activity against multidrug-resistant bacteria. The researchers noted that the Fmoc protection strategy allowed for the precise control of peptide sequence and conformation, which is critical for optimizing antimicrobial efficacy.

Despite its widespread use, challenges remain in the handling and storage of Fmoc-l-alanyl Chloride due to its sensitivity to moisture and heat. Recent advancements in reagent formulation, such as the development of stabilized derivatives, have addressed some of these issues. A 2023 patent application disclosed a novel formulation of Fmoc-l-alanyl Chloride with improved shelf-life and handling properties, which could further streamline its application in large-scale peptide synthesis.

In conclusion, Fmoc-l-alanyl Chloride (CAS: 103321-50-2) continues to be a cornerstone in peptide chemistry, with emerging applications in drug delivery, antimicrobial therapy, and bioconjugation. Ongoing research and technological innovations are expected to expand its utility and address current limitations, solidifying its position as an indispensable tool in chemical biology and pharmaceutical development.

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