S-(9-Fluolenylmethyl)-L-cysteine
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S-(9-Fluolenylmethyl)-L-cysteine

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Category
L-Amino Acids
Catalog number
BAT-006064
CAS number
84888-38-0
Molecular Formula
C17H17NO2S
Molecular Weight
299.39
S-(9-Fluolenylmethyl)-L-cysteine
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
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.
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