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Application Area

Fmoc-Ala(2-Pyr-4-Cl)-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-008703

CAS number

2350007-37-1

Molecular Formula

C23H19ClN2O4

Molecular Weight

422.86

IUPAC Name

(2S)-3-(4-chloropyridin-2-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

Synonyms

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-chloropyridin-2-yl)propanoic acid

Purity

98.0%

Density

1.370±0.06 g/cm3

Boiling Point

644.6±55.0 °C at 760 mmHg

InChI

InChI=1S/C23H19ClN2O4/c24-14-9-10-25-15(11-14)12-21(22(27)28)26-23(29)30-13-20-18-7-3-1-5-16(18)17-6-2-4-8-19(17)20/h1-11,20-21H,12-13H2,(H,26,29)(H,27,28)/t21-/m0/s1

InChI Key

XPZUFCQFKKGOAX-NRFANRHFSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=NC=CC(=C4)Cl)C(=O)O

Fmoc-Ala(2-Pyr-4-Cl)-OH, a specialized amino acid utilized in peptide synthesis, holds a wide array of applications in both research and pharmaceutical domains. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in solid-phase peptide synthesis, Fmoc-Ala(2-Pyr-4-Cl)-OH plays a pivotal role in the precise construction of peptides with tailored sequences and functionalities. Harnessing the Fmoc protective group, researchers can systematically assemble peptides, seamlessly integrating this modified amino acid into investigations exploring intricate structure-activity relationships and the evolution of therapeutic peptides.

Drug Development: Positioned at the forefront of pharmaceutical research, this compound is instrumental in crafting peptide-based medications. The distinct side chain modification augments pharmacokinetic properties such as stability and bioavailability, key factors in customizing peptides as enzymatic inhibitors, receptor ligands, or antimicrobial agents. This breakthrough in drug discovery propels advancements in the medical realm, driving innovation and progress.

Bioconjugation: Within the realm of bioconjugation strategies, Fmoc-Ala(2-Pyr-4-Cl)-OH emerges as a pivotal component for linking peptides to a myriad of molecules ranging from antibodies to nanoparticles. This fusion enhances the functional attributes of peptides, leading to targeted delivery mechanisms and heightened efficacy in therapeutic applications. The integration of this modified amino acid in bioconjugation endeavors fosters ingenuity in drug delivery techniques and diagnostic methodologies.

Protein Engineering: In the landscape of protein engineering, the integration of modified amino acids like Fmoc-Ala(2-Pyr-4-Cl)-OH harbors the potential to revolutionize protein characteristics. Researchers can introduce these alterations to unravel the intricacies of protein folding, stability, and interactions, pivotal in crafting proteins with amplified functionalities for industrial and therapeutic pursuits. This innovative approach in protein design heralds a new era of possibilities in advancing protein engineering practices.

1. Novel complexes of Co(III) and Ni(II) containing peptide ligands: synthesis, DNA binding and photonuclease activity

C N Sudhamani, H S Bhojya Naik, D Girija, K R Sangeetha Gowda, M Giridhar, T Arvinda Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 24;118:271-8. doi: 10.1016/j.saa.2013.08.074. Epub 2013 Aug 31.

The new cobalt(III) and nickel(II) complexes of the type [M(L)2(H2O)2](n)(+) (where M = Co(III) or Ni(II) ion, n = 3 for Co and 2 for Ni, L = peptides Fmoc. Ala-val-OH (F-AVOH), Fmoc-Phe-Leu-Ome (F-PLOMe) and Z-Ala-Phe-CONH2 (Z-APCONH2)) were synthesized and structurally characterized by FTIR, (1)H NMR, elemental analysis and electronic spectral data. An octahedral geometry has been proposed for all the synthesized Co(III) and Ni(II) metal complexes. The binding property of the complexes with CT-DNA was studied by absorption spectral analysis, followed by viscosity measurement and thermal denaturation studies. Detailed analysis revealed that the metal complexes intercalates into the DNA base stack as intercalator. The photo induced cleavage studies shows that the complexes possess photonuclease property against pUC19 DNA under UV-Visible irradiation.

2. High-Quality Conjugated Polymers Achieving Ultra-Trace Detection of Cr2O72- in Agricultural Products

Hui Li, Fei Li, Fang Liu, Xiao Chen, Wenyuan Xu, Liang Shen, Jingkun Xu, Rui Yang, Ge Zhang Molecules. 2022 Jul 4;27(13):4294. doi: 10.3390/molecules27134294.

In view of that conjugated polymers (CPs) are an attractive option for constructing high-sensitive Cr2O72- sensors but suffer from lacking a general design strategy, we first proposed a rational structure design of CPs to tailor their sensing properties while validating the structure-to-performance correlation. Short side chains decorated with N and O atoms as recognition groups were instructed into fluorene to obtain monomers Fmoc-Ala-OH and Fmoc-Thr-OH. Additionally, their polymers P(Fmoc-Ala-OH) and P(Fmoc-Thr-OH) were obtained through electrochemical polymerization. P(Fmoc-Ala-OH) and P(Fmoc-Thr-OH) with high polymerization degrees have an excellent selectivity towards Cr2O72- in comparison to other cations and anions. Additionally, their limit of detection could achieve 1.98 fM and 3.72 fM, respectively. Especially, they could realize the trace detection of Cr2O72- in agricultural products (red bean, black bean, and millet). All these results indicate that short side chains decorated with N and O atoms functionalizing polyfluorene enables the ultra-trace detection of Cr2O72-. Additionally, the design strategy will spark new ideas for the construction of highly selective and sensitive Cr2O72- sensors.

3. Identification of Fmoc-beta-Ala-OH and Fmoc-beta-Ala-amino acid-OH as new impurities in Fmoc-protected amino acid derivatives

E Hlebowicz, A J Andersen, L Andersson, B A Moss J Pept Res. 2005 Jan;65(1):90-7. doi: 10.1111/j.1399-3011.2004.00201.x.

During the manufacture of a proprietary peptide drug substance a new impurity appeared unexpectedly. Investigation of its chemical structure established the impurity as a beta-Ala insertion mutant of the mother peptide. The source of the beta-Ala was identified as contamination of the Fmoc-Ala-OH raw material with Fmoc-beta-Ala-Ala-OH. Further studies also demonstrated the presence of beta-Ala in other Fmoc-amino acids, particularly in Fmoc-Arg(Pbf)-OH. In this case, it was due to the presence of both Fmoc-beta-Ala-OH and Fmoc-beta-Ala-Arg(Pbf)-OH. It is concluded that beta-Ala contamination of Fmoc-amino acid derivatives is a general and hitherto unrecognized problem to suppliers of Fmoc-amino acid derivatives. The beta-Ala is often present as Fmoc-beta-Ala-OH and/or as a dipeptide, Fmoc-beta-Ala-amino acid-OH. In collaboration with the suppliers, new specifications were introduced, recognizing the presence of beta-Ala-related impurities in the raw materials and limiting them to acceptable levels. The implementation of these measures has essentially eliminated beta-Ala contamination as a problem in the manufacture of the drug substance.