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Application Area

Fmoc-D-Cys(Me)-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-001918

CAS number

1393524-09-8

Molecular Formula

C19H19NO4S

Molecular Weight

357.4

IUPAC Name

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylsulfanylpropanoic acid

Synonyms

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methylsulfanylpropanoic acid

InChI

InChI=1S/C19H19NO4S/c1-25-11-17(18(21)22)20-19(23)24-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,16-17H,10-11H2,1H3,(H,20,23)(H,21,22)/t17-/m1/s1

InChI Key

SKNJDZVHMNQAGO-QGZVFWFLSA-N

Canonical SMILES

CSCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-D-Cys(Me)-OH, a derivative of cysteine utilized in peptide synthesis, boasts a range of critical applications in bioscience. Here are four key applications:

Peptide Synthesis: Serving as a foundational component in peptide synthesis, Fmoc-D-Cys(Me)-OH enables the creation of peptides with tailored functions and properties. Its inclusion allows for the integration of methylated cysteine residues, which can modulate the biological activity and stability of the peptide. This capability is essential for crafting peptides tailored for research, therapeutic, and diagnostic purposes, expanding the horizons of peptide-based applications.

Drug Development: Driving innovation in drug development, Fmoc-D-Cys(Me)-OH plays a pivotal role in the design and synthesis of peptides that mimic protein-protein interactions. These peptides serve as effectual inhibitors or activators of target proteins, offering promising therapeutic advantages. Through the addition of a methyl group, the selectivity and potency of peptide-based drugs can be enhanced, propelling the evolution of precision medicine and targeted therapies.

Bioconjugation: Positioned at the forefront of bioconjugation techniques, Fmoc-D-Cys(Me)-OH facilitates the linking of peptides to diverse molecules such as proteins, drugs, or imaging agents. The presence of the methyl group improves the stability of the conjugate and mitigates unwanted side reactions, fostering the development of cutting-edge molecular probes and refined targeted delivery systems. This application stands as a cornerstone in advancing the field of molecular engineering and precision medicine.

Structural Biology: Enabling groundbreaking studies in structural biology, researchers leverage Fmoc-D-Cys(Me)-OH to delve into the influence of methylation on protein and peptide folding. This investigation sheds light on how methylation impacts conformational dynamics, protein interactions, and overall molecular behavior. The insights gained from these studies inform the design of superior therapeutic proteins and peptides, driving forward the frontiers of structural biology and precision medicine.

1. Low-Dimensional Architectures in Isomeric cis-PtCl2{Ph2PCH2N(Ar)CH2PPh2} Complexes Using Regioselective-N(Aryl)-Group Manipulation

Peter De'Ath, Mark R J Elsegood, Noelia M Sanchez-Ballester, Martin B Smith Molecules. 2021 Nov 11;26(22):6809. doi: 10.3390/molecules26226809.

The solid-state behaviour of two series of isomeric, phenol-substituted, aminomethylphosphines, as the free ligands and bound to PtII, have been extensively studied using single crystal X-ray crystallography. In the first library, isomeric diphosphines of the type Ph2PCH2N(Ar)CH2PPh2 [1a-e; Ar = C6H3(Me)(OH)] and, in the second library, amide-functionalised, isomeric ligands Ph2PCH2N{CH2C(O)NH(Ar)}CH2PPh2 [2a-e; Ar = C6H3(Me)(OH)], were synthesised by reaction of Ph2PCH2OH and the appropriate amine in CH3OH, and isolated as colourless solids or oils in good yield. The non-methyl, substituted diphosphines Ph2PCH2N{CH2C(O)NH(Ar)}CH2PPh2 [2f, Ar = 3-C6H4(OH); 2g, Ar = 4-C6H4(OH)] and Ph2PCH2N(Ar)CH2PPh2 [3, Ar = 3-C6H4(OH)] were also prepared for comparative purposes. Reactions of 1a-e, 2a-g, or 3 with PtCl2(η4-cod) afforded the corresponding square-planar complexes 4a-e, 5a-g, and 6 in good to high isolated yields. All new compounds were characterised using a range of spectroscopic (1H, 31P{1H}, FT-IR) and analytical techniques. Single crystal X-ray structures have been determined for 1a, 1b∙CH3OH, 2f∙CH3OH, 2g, 3, 4b∙(CH3)2SO, 4c∙CHCl3, 4d∙½Et2O, 4e∙½CHCl3∙½CH3OH, 5a∙½Et2O, 5b, 5c∙¼H2O, 5d∙Et2O, and 6∙(CH3)2SO. The free phenolic group in 1b∙CH3OH, 2f∙CH3OH,2g, 4b∙(CH3)2SO, 5a∙½Et2O, 5c∙¼H2O, and 6∙(CH3)2SO exhibits various intra- or intermolecular O-H∙∙∙X (X = O, N, P, Cl) hydrogen contacts leading to different packing arrangements.

2. Geometric and electronic structures of phenoxyl radicals hydrogen bonded to neutral and cationic partners

Maylis Orio, Olivier Jarjayes, Benoit Baptiste, Christian Philouze, Carole Duboc, Jenny-Lee Mathias, Laurent Benisvy, Fabrice Thomas Chemistry. 2012 Apr 23;18(17):5416-29. doi: 10.1002/chem.201102854. Epub 2012 Mar 13.

Two di-tert-butylphenols incorporating an N-methylbenzimidazole moiety in the ortho or para position have been synthesised ((Me)OH and (pMe)OH, respectively). Their X-ray structures evidence a hydrogen bond between the phenolic proton and the iminic nitrogen atom, whose nature is intra- and intermolecular, respectively. The present studies demonstrate that (Me)OH is readily oxidised by an intramolecular PET mechanism to form the hydrogen-bonded phenoxyl-N-methylbenzimidazolium system ((Me)OH)(.+) , whereas oxidation of (pMe)OH occurs by intermolecular PET, affording the neutral phenoxyl benzimidazole ((pMe)O)(.) system. The deprotonations of (Me)OH and (pMe)OH yield the corresponding phenolate species ((Me)O)(-) and ((pMe)O)(-), respectively, whilst that of the previously reported (H)OH (analogous to (Me)OH but lacking the N-methyl group) produces an unprecedented hydrogen-bonded phenol benzimidazolate species, as evidenced by its X-ray structure. The latter is believed to be in equilibrium in solution with its tautomeric phenolate form, as suggested by NMR, electrochemistry and DFT studies. The one-electron oxidations of the anions occur by a simple ET process affording phenoxyl radical species, whose electronic structure has been studied by HF-EPR spectroscopy and DFT calculations. In particular, analysis of the g(1) tensor shows the order 2.0079>2.0072>2.0069>2.0067 for ((Me)O)(.), ((H)O)(.), ((Me)OH)(.+) and ((H)OH)(.+), respectively. ((Me)O)(.) exhibits the largest g(1) tensor (2.0079), consistent with the absence of intramolecular hydrogen bond. The g(1) tensor of ((H)O)(.) is intermediate between those of ((Me)OH)(.+) and ((Me)O)(.) (g(1)=2.0072), indicating that the phenoxyl oxygen is hydrogen-bonded with a neutral benzimidazole partner.