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S-(9-Fluolenylmethyl)-L-cysteine

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

Category

L-Amino Acids

Catalog number

BAT-006064

CAS number

84888-38-0

Molecular Formula

C17H17NO2S

Molecular Weight

299.39

IUPAC Name

(2R)-2-amino-3-(9H-fluoren-9-ylmethylsulfanyl)propanoic acid

Synonyms

H-Cys(Fm)-OH

InChI

InChI=1S/C17H17NO2S/c18-16(17(19)20)10-21-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10,18H2,(H,19,20)/t16-/m0/s1

InChI Key

SFRBQYRAZQGDPW-INIZCTEOSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)CSCC(C(=O)O)N

S-(9-Fluorenylmethyl)-L-cysteine, a specialized reagent pivotal in peptide synthesis and bioconjugation, finds diverse applications in the realm of molecular chemistry. Here are four key applications:

Peptide Synthesis: Serving as a cornerstone in solid-phase peptide synthesis, this compound emerges as a crucial element as a protected cysteine derivative. Its role in averting undesired side reactions during peptide elongation is paramount. Upon deprotection, the cysteine residues become available for forging disulfide bonds, crucial for attaining the precise peptide conformation.

Protein-Drug Conjugates: Nestled at the intersection of protein chemistry and pharmacology, S-(9-Fluorenylmethyl)-L-cysteine acts as a vital linkage in the creation of protein-drug conjugates. By binding drugs to specific cysteine residues on proteins, researchers fashion targeted therapeutics boasting enhanced efficacy and diminished side effects. This strategy proves particularly valuable in crafting antibody-drug conjugates tailored for cutting-edge cancer therapies.

Bioconjugation: Within the intricate domain of bioconjugation chemistry, S-(9-Fluorenylmethyl)-L-cysteine takes center stage in introducing reactive thiol groups into peptides and proteins. These thiol groups, in turn, engage in subsequent conjugation reactions such as synthesizing enzyme-label conjugates or anchoring biomolecules to surfaces. This process stands as a linchpin for a myriad of diagnostic and therapeutic endeavors, driving innovations in healthcare.

Structural Biology: Delving into the realm of structural biology, the incorporation of S-(9-Fluorenylmethyl)-L-cysteine plays a pivotal role in fortifying proteins and peptides through the formation of disulfide bonds. By implanting protected cysteine residues, scientists can manipulate folding pathways and investigate the structural boundaries imposed by disulfide bridges. This quest yields profound insights into protein folding mechanisms and structural integrity, shedding light on the intricacies of molecular architecture.

1. S-Nitroso-l-cysteine and ventilatory drive: A pediatric perspective

Dallin Hubbard, Kaylee Tutrow, Benjamin Gaston Pediatr Pulmonol. 2022 Oct;57(10):2291-2297. doi: 10.1002/ppul.26036. Epub 2022 Jul 24.

Though endogenous S-nitroso-l-cysteine (l-CSNO) signaling at the level of the carotid body increases minute ventilation (v̇E ), neither the background data nor the potential clinical relevance are well-understood by pulmonologists in general, or by pediatric pulmonologists in particular. Here, we first review how regulation of the synthesis, activation, transmembrane transport, target interaction, and degradation of l-CSNO can affect the ventilatory drive. In particular, we review l-CSNO formation by hemoglobin R to T conformational change and by nitric oxide (NO) synthases (NOS), and the downstream effects on v̇E through interaction with voltage-gated K+ (Kv) channel proteins and other targets in the peripheral and central nervous systems. We will review how these effects are independent of-and, in fact may be opposite to-those of NO. Next, we will review evidence that specific elements of this pathway may underlie disorders of respiratory control in childhood. Finally, we will review the potential clinical implications of this pathway in the development of respiratory stimulants, with a particular focus on potential pediatric applications.

2. Derivatives of S-9-fluorenylmethyl-L-cysteine

M Bodanszky, M A Bednarek Int J Pept Protein Res. 1982 Nov;20(5):434-7. doi: 10.1111/j.1399-3011.1982.tb03064.x.

The 9-fluorenylmethyl (Fm) group was examined with respect to its potential for blocking the sulfhydryl function. The S-Fm group is resistant to acids and to catalytic hydrogenation but is cleaved by ammonia in methanol or by organic bases, such as a 20% solution of piperidine in dimethylformamide. Synthesis of N-tert.-butyloxycarbonyl-S-9-fluorenylmethyl-L-cysteine p-nitrophenyl ester and of cysteinyl peptides protected with the S-Fm group are described.

3. S-carboxymethyl-L-cysteine

Steve C Mitchell, Glyn B Steventon Drug Metab Rev. 2012 May;44(2):129-47. doi: 10.3109/03602532.2011.631015.

S-carboxymethyl-L-cysteine, the side-chain carboxymethyl derivative of the sulfur-containing amino acid, cysteine, has been known and available for almost 80 years. During this time, it has been put to a variety of uses, but it is within the field of respiratory medicine that, presently, it has found a clinical niche. Early studies indicated that this compound underwent a rather simplistic, predictable pattern of metabolism, whereas later investigations alluded to more subtle interactions with the pathways of intermediary metabolism, as may be expected for an amino acid derivative. In addition, suggestions of polymorphic influences and circadian rhythms within metabolic profiles have emerged. These latter factors may underlie the conflicting reports regarding the therapeutic efficacy of this compound: that it appears to work well in some patients, but has no measurable effects in others. The relevant literature pertaining to the fate of this compound within living systems has been reviewed and a comprehensive précis advanced. Hopefully, this article will serve as a vade mecum for those interested in S-carboxymethyl-L-cysteine and as a catalyst for future research.