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Application Area

Fmoc-N-Me-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-008505

CAS number

481642-17-5

Molecular Formula

C20H21NO4S

Molecular Weight

371.5

IUPAC Name

2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-methylsulfanylpropanoic acid

Synonyms

Fmoc-DL-N(Me)Cys(Me)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N,S-dimethyl-L-Cysteine

InChI

InChI=1S/C20H21NO4S/c1-21(18(12-26-2)19(22)23)20(24)25-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,17-18H,11-12H2,1-2H3,(H,22,23)

InChI Key

GHJZJWOYPATEAL-UHFFFAOYSA-N

Canonical SMILES

CN(C(CSC)C(=O)O)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-N-Me-Cys(Me)-OH stands as a modified amino acid derivative utilized in peptide synthesis and a multitude of biochemical research applications. Here are four key applications of Fmoc-N-Me-Cys(Me)-OH:

Peptide Synthesis: In the realm of solid-phase peptide synthesis (SPPS), Fmoc-N-Me-Cys(Me)-OH emerges as a pivotal player, facilitating the efficient assembly of peptides endowed with specific structural characteristics. The Fmoc group acts as a shield, safeguarding the amino acid throughout the synthesis procedure, ensuring its precise integration into the peptide chain. This capability empowers researchers to fashion tailored peptides for delving into protein-protein interactions, enzyme functionalities, and potential therapeutic utilities, crafting a profound understanding of molecular interplay.

Protein Engineering: Within the domain of protein engineering, this modified amino acid plays a significant role, enabling the incorporation of non-standard amino acids to scrutinize the intricate structure-function dynamics of proteins. Fmoc-N-Me-Cys(Me)-OH can introduce distinctive side chains or functional groups into proteins, exerting influence over protein folding, stability, and activity. These modifications stand as linchpins in the creation of novel proteins imbued with desired attributes for applications spanning industrial, medical, and research spheres.

Drug Development: Positioned at the forefront of pharmaceutical research, Fmoc-N-Me-Cys(Me)-OH emerges as a linchpin in crafting peptide-based therapeutics characterized by heightened stability and efficacy. Via the integration of modified amino acids like Fmoc-N-Me-Cys(Me)-OH, therapeutic peptides can be honed to withstand enzymatic degradation and enhance binding specificity, honing in on precise disease targets with surgical precision. This application holds paramount significance in tailoring therapeutic interventions to address specific ailments with unparalleled precision.

Chemical Biology: Embraced by the realm of chemical biology, Fmoc-N-Me-Cys(Me)-OH finds utility in dissecting cellular processes and dynamics with finesse. By seamlessly integrating this modified amino acid into peptides, scientists harness these peptides as molecular instruments to unravel biological pathways and interactions within living cells. This methodology affords researchers the tools to visualize and manipulate cellular machinery, unravelling the intricacies of biological systems and catapulting our comprehension of the elaborate tapestry of life.

2. 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.

3. Mechanism of O2 activation and methanol production by (di(2-pyridyl)methanesulfonate)Pt(II)Me(OH(n))((2-n)-) complex from theory with validation from experiment

Wei-Guang Liu, Anna V Sberegaeva, Robert J Nielsen, William A Goddard 3rd, Andrei N Vedernikov J Am Chem Soc. 2014 Feb 12;136(6):2335-41. doi: 10.1021/ja409036c. Epub 2014 Feb 3.

The mechanism of the (dpms)Pt(II)Me(OH(n))((2-n)-) oxidation in water to form (dpms)Pt(IV)Me(OH)2 and (dpms)Pt(IV)Me2(OH) complexes was analyzed using DFT calculations. At pH < 10, (dpms)Pt(II)Me(OH(n))((2-n)-) reacts with O2 to form a methyl Pt(IV)-OOH species with the methyl group trans to the pyridine nitrogen, which then reacts with (dpms)Pt(II)Me(OH(n))((2-n)-) to form 2 equiv of (dpms)Pt(IV)Me(OH)2, the major oxidation product. Both the O2 activation and the O-O bond cleavage are pH dependent. At higher pH, O-O cleavage is inhibited whereas the Pt-to-Pt methyl transfer is not slowed down, so making the latter reaction predominant at pH > 12. The pH-independent Pt-to-Pt methyl transfer involves the isomeric methyl Pt(IV)-OOH species with the methyl group trans to the sulfonate. This methyl Pt(IV)-OOH complex is more stable and more reactive in the Pt-to-Pt methyl-transfer reaction as compared to its isomer with the methyl group trans to the pyridine nitrogen. A similar structure-reactivity relationship is also observed for the S(N)2 functionalization to form methanol by two isomeric (dpms)Pt(IV)Me(OH)2 complexes, one featuring the methyl ligand trans to the sulfonate group and another with the methyl trans to the pyridine nitrogen. The barrier to functionalize the former isomer with the CH3 group trans to the sulfonate group is 2-9 kcal/mol lower. The possibility of the involvement of Pt(III) species in the reactions studied was found to correspond to high-barrier reactions and is hence not viable. It is concluded that the dpms ligand facilitates Pt(II) oxidation both enthalpically and entropically.