N-Fmoc-L-cysteine
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N-Fmoc-L-cysteine

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N-Fmoc-L-cysteine is the N-Fmoc-protected form of L-Cysteine, a non-essential α-amino acid that is biosynthesized in humans. L-Cysteine is also a bicarbonate-sensitive endogenous excitotoxin in rats and possibly humans.

Category
Fmoc-Amino Acids
Catalog number
BAT-005302
CAS number
135248-89-4
Molecular Formula
C18H17NO4S
Molecular Weight
343.40
N-Fmoc-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-sulfanylpropanoic acid
Synonyms
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-cysteine; Fmoc-L-Cys-OH; Fmoc-cysteine; N-(9-Fluorenylmethoxycarbonyl)cysteine
Appearance
White to Off-White Solid
Purity
96%
Density
1.337±0.06 g/cm3(Predicted)
Melting Point
98-102ºC
Boiling Point
574.4±50.0 °C(Predicted)
Storage
Store at -20°C, under inert atmosphere
Solubility
soluble in Acetone, DMF, DMSO, Methanol
InChI
InChI=1S/C18H17NO4S/c20-17(21)16(10-24)19-18(22)23-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16,24H,9-10H2,(H,19,22)(H,20,21)/t16-/m0/s1
InChI Key
RMTDKXQYAKLQKF-INIZCTEOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CS)C(=O)O
1. Development of a sensitive, rapid, biotin-streptavidin based chemiluminescent enzyme immunoassay for human thyroid stimulating hormone
Zhen Lin, Xu Wang, Zhen-Jia Li, Shi-Qi Ren, Guo-Nan Chen, Xi-Tang Ying, Jin-Ming Lin Talanta. 2008 May 30;75(4):965-72. doi: 10.1016/j.talanta.2007.12.043. Epub 2008 Jan 6.
A highly sensitive "two-site" chemiluminescent immunoassay specific for human thyroid stimulating hormone (TSH) was developed. The signal amplification was achieved via a biotin-streptavidin system (BSAS). The HRP-luminol-H(2)O(2) chemiluminescent system with high sensitivity was chosen as the detection system. Biotinylated anti-TSH monoclonal antibody (MAb) and HRP-labeled streptavidin were first synthesized. Then the signal amplification was achieved through the interaction between the biotinylated anti-TSH MAb and the HRP-streptavidin conjugate. The light intensity developed was in proportion to the TSH present in the samples. The assay showed little cross-reactivity with three other glycoprotein hormones (human chorionic gonadotropin (HCG), luteinizing hormone (LH), follicle stimulating hormone (FSH)) due to the high specificity of the antibody. The working range for human thyroid stimulating hormone was 0.1-40 mU L(-1). Both the intra-assay and inter-assay coefficients of variation were less than 10% for the BSAS based chemiluminescent enzyme immunoassay (CLEIA). The proposed assay had a sensitivity of 0.01 mU L(-1) which was 10-fold higher than the HRP-MAb conjugate based TSH immunoassay. Thus the higher sensitivity facilitated the clinical testing for thyroid states. The effects of several reaction parameters, such as incubation time, temperature, and reaction volume of the method, were also studied. This method has been successfully applied to the evaluation of TSH in human serum. Compared with the commercial enzyme chemiluminescent immunoassay, the correlation was satisfied.
2. [Antibody engineering-based approach for hapten immunometric assays with high sensitivity]
Norihiro Kobayashi, Yoshinori Kato, Hiroyuki Oyama, Junichi Goto Yakugaku Zasshi. 2007 Jan;127(1):55-69. doi: 10.1248/yakushi.127.55.
The trace characterization of physiologically active substances with low molecular weight (e.g., steroids, catecholamines, prostaglandins, and oligopeptides), which are classified as "haptens", is an important subject in clinical analysis, and competitive immunoassays have conventionally been used for this purpose. However, the subfemtomole-range determination of haptens is very difficult, as the sensitivity of competitive immunoassays is essentially limited by the affinity of the anti-hapten antibodies that barely reaches the range of 10(11) (l/mol) as the affinity constant (K(a)). Although a noncompetitive "immunometric assay" format, the two-site immunometric assay (sandwich immunoassay), enables even subattomole-range measurements of macromolecules such as proteins, this principle can not be directly applied to haptens, as their low molecular mass prohibits simultaneous binding by two antibody molecules. To overcome such limitations, we are required either to create artificial antibodies showing ultrahigh affinity to haptens by protein engineering of antibody molecules ("antibody engineering") or establishment of novel immunometric assay formats applicable to haptens. This review surveys the background and recent approach for subfemtomole-range determination of haptens using novel immunometric assay methods. Our studies for the development of hapten immunometric assays are also described.
3. Monoclonal antibodies generated against an affinity-labeled immune complex of an anti-bile acid metabolite antibody: an approach to noncompetitive hapten immunoassays based on anti-idiotype or anti-metatype antibodies
N Kobayashi, H Oiwa, K Kubota, S Sakoda, J Goto J Immunol Methods. 2000 Nov 1;245(1-2):95-108. doi: 10.1016/s0022-1759(00)00291-x.
Conventional immunoassays for haptens such as steroids and synthetic drugs are dependent on the competitive reaction between an unlabeled antigen (analyte) and a labeled antigen against a limited amount of anti-hapten antibody. Although noncompetitive immunoassay procedures such as two-site immunometric assays offer a much higher sensitivity, direct application of this principle to haptens has been difficult due to their small molecular mass precluding simultaneous binding by two antibody molecules. Here, we have attempted to develop a noncompetitive immunoassay system based on anti-idiotype or anti-metatype antibodies. Ursodeoxycholic acid 7-N-acetylglucosaminide (UDCA 7-NAG), which is a bile acid metabolite (molecular weight, 595.8), was selected as the model hapten. A/J mice were immunized with a monoclonal antibody against UDCA 7-NAG, which had been affinity-labeled with a relevant hapten derivative. The fusion between the immune spleen cells and P3/NS1/1-Ag4-1 myeloma cells yielded four kinds of alpha-type and two kinds of beta-type monoclonal anti-idiotype antibodies, each recognizing the framework region and paratope of the anti-hapten antibody. The use of a selected combination between alpha-type and beta-type antibodies together with the anti-hapten antibody provided a noncompetitive assay system with a subfemtomole order sensitivity (detection limit, 118 amol) and a practical specificity.
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