S-Diphenylmethyl-L-cysteine
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S-Diphenylmethyl-L-cysteine

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The S-diphenylmethyl group is one of the most effective S-protecting groups for cysteine.

Category
L-Amino Acids
Catalog number
BAT-004199
CAS number
5191-80-0
Molecular Formula
C16H17NO2S
Molecular Weight
287.38
S-Diphenylmethyl-L-cysteine
IUPAC Name
(2R)-2-amino-3-benzhydrylsulfanylpropanoic acid
Synonyms
L-Cys(Dpm)-OH; (R)-2-Amino-3-(Benzhydrylthio)Propanoic Acid
Appearance
White powder
Purity
≥ 99% (TLC)
Density
1.24 g/cm3
Melting Point
195-208 °C
Boiling Point
455.5°C
Storage
Store at RT
InChI
InChI=1S/C16H17NO2S/c17-14(16(18)19)11-20-15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14-15H,11,17H2,(H,18,19)/t14-/m0/s1
InChI Key
SHOGZCIBPYFZRP-AWEZNQCLSA-N
Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)SCC(C(=O)O)N

S-Diphenylmethyl-L-cysteine is an organic compound recognized for its specific molecular configuration and unique properties. Structurally, it is an L-cysteine derivative where a diphenylmethyl group is attached to the sulfur atom of the cysteine, distinguishing it from other cysteine derivatives. This modification offers distinct physiochemical characteristics, making S-Diphenylmethyl-L-cysteine an intriguing subject in chemical and pharmaceutical research. The compound is often explored for its potential biological activity, given that the L-form of cysteine is naturally occurring and biologically significant. Understanding the nature of S-Diphenylmethyl-L-cysteine lays the foundation for its diverse applications across multiple fields.

One of the paramount applications of S-Diphenylmethyl-L-cysteine is in the field of medicinal chemistry, particularly in drug design and development. The unique structure of this compound allows it to interact with biological systems in potentially beneficial ways, such as acting as a precursor or an active agent within pharmaceutical formulations. Researchers investigate its utility in developing drugs that can modulate biological pathways, potentially offering therapeutic benefits for conditions that are currently hard to treat. Its applications in this field are underscored by the ongoing demand for innovative compounds that can lead to the development of more effective and targeted therapies.

In the realm of organic synthesis, S-Diphenylmethyl-L-cysteine serves as a valuable chiral building block. Chirality is a fundamental property in chemistry that can influence the pharmacodynamics and pharmacokinetics of therapeutic agents. As such, chiral compounds are highly sought after for synthesizing complex molecules, including those necessary for creating enantiomerically pure pharmaceuticals. The presence of both the diphenylmethyl and the cysteine moiety provides a useful scaffold that chemists can exploit to construct new molecules with high precision and desired biological activity. This application emphasizes the strategic role of S-Diphenylmethyl-L-cysteine in advancing synthetic methodologies.

Another critical area of application is materials science, where S-Diphenylmethyl-L-cysteine is investigated for its potential in developing novel materials with specific functional properties. The compound’s unique chemical structure allows it to potentially impart desirable characteristics, such as enhanced stability or specific electronic properties, to materials. Such applications are valuable in the production of polymers, nanomaterials, or surface coatings that require precise molecular engineering. Through careful manipulation of its properties, S-Diphenylmethyl-L-cysteine can contribute to the advancement of materials technology, bringing about innovations that can be applied in various technological industries.

Lastly, S-Diphenylmethyl-L-cysteine is relevant in biochemical research, particularly in studying protein and enzyme interactions. By serving as a model compound, it aids in understanding how structural modifications can influence protein function, which is crucial for elucidating the mechanisms of enzyme activity and protein folding. This application holds significance for both basic science and applied research, providing insights that could lead to the development of new strategies for manipulating protein function in therapeutic contexts. The ability to influence protein interactions through designed compounds like S-Diphenylmethyl-L-cysteine underscores its importance in the landscape of biochemical investigations.

1. Dynamic ligand-exchange chiral stationary phase from S-benzyl-(R)-cysteine
B Natalini, R Sardella, A Macchiarulo, R Pellicciari Chirality. 2006 Aug;18(7):509-18. doi: 10.1002/chir.20280.
S-benzyl-(R)-cysteine (R-SBC) is a new chiral ligand-exchange stationary phase which has proved to be effective in the analytical separation of some natural and unnatural underivatized amino acids with fair to good separation and resolution factors. The dynamic coating of the RP-18 solid support with S-Benzyl-(R)-cysteine (R-SBC) gives rise to a stable and efficient chiral stationary phase (CSP) that has been successfully employed. The mechanism of chiral recognition is discussed and a molecular modeling study aimed at identifying molecular descriptors responsible for observed different behaviours of analytes upon different albeit closely related selectors is discussed.
2. Descriptive structure-separation relationship studies in chiral ligand-exchange chromatography
Benedetto Natalini, Antonio Macchiarulo, Roccaldo Sardella, Alberto Massarotti, Roberto Pellicciari J Sep Sci. 2008 Jul;31(13):2395-403. doi: 10.1002/jssc.200800102.
A new approach to model and interpret the separation of amino acid enantiomers is described. The descriptive structure-separation relationship (DSSR) study of a set of amino acid enantiomer couples analyzed with two chiral selectors S-benzyl-(R)-cysteine ((R)-SBC) and S-trityl-(R)-cysteine ((R)-STC) has been performed with the aim to highlight the molecular properties of the analyte affecting the enantiodiscrimination process. Although with some exceptions, the classification models obtained with (R)-STC indicate that the partial positive surface area (PPSA-1) is the suitable descriptor to account for the separation of both (R)- and (S)-enantiomers. On the other hand, two different descriptors characterize the separation process with (R)-SBC. While fractional negatively charged partial surface area (FNSA-3) results the discriminating descriptor for (R)-enantiomers, the relative polar surface area (RPSA) is able to best discriminate among (S)-enantiomers.
3. S-trityl-(R)-cysteine, a powerful chiral selector for the analytical and preparative ligand-exchange chromatography of amino acids
Benedetto Natalini, Roccaldo Sardella, Antonio Macchiarulo, Roberto Pellicciari J Sep Sci. 2008 Mar;31(4):696-704. doi: 10.1002/jssc.200700511.
S-trityl-(R)-cysteine [(R)-STC] is the new selector of a dynamically coated, chiral ligand-exchange stationary phase which proved to be highly effective in both analytical and preparative-scale separation of enantiomers of some natural and unnatural underivatized amino acids, with good separation and resolution factors. With the aim of identifying the best chromatographic conditions suitable for the preparative-scale separations, some parameters controlling retention, separation and resolution factors (such as the type and amount of cupric salt and the eluent pH) were investigated. The relatively easy removal of the Cu(II) ions renders this technique suitable for obtaining small amounts of enantiomerically pure samples for preliminary biological evaluations.
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