71989-26-9 Usage
Description
N-alpha-FMOC-Nepsilon-BOC-L-Lysine, also known as Fmoc-Lys(Boc)-OH, is a protected amino acid derivative that plays a crucial role in the synthesis of various bioactive compounds and drug delivery systems. It is characterized by the presence of two protecting groups, the 9-fluorenylmethoxycarbonyl (Fmoc) group at the alpha-amino group and the tert-butyloxycarbonyl (Boc) group at the epsilon-amino group of the lysine side chain. These protecting groups ensure the selective deprotection and coupling of the amino acid during peptide synthesis, making it a versatile building block for the development of complex peptide-based structures.
Uses
Used in Pharmaceutical Industry:
N-alpha-FMOC-Nepsilon-BOC-L-Lysine is used as a key intermediate in the solid-phase synthesis of dimeric RGD peptide-paclitaxel conjugates, which serve as a model for integrin-targeted drug delivery. This targeted approach allows for the efficient delivery of therapeutic agents, such as paclitaxel, to cancer cells, minimizing side effects and improving treatment outcomes.
Used in Biomedical Research:
In the field of biomedical research, N-alpha-FMOC-Nepsilon-BOC-L-Lysine is utilized for the synthesis of DOTA-conjugated multivalent cyclic-RGD peptide dendrimers. These dendrimers are designed for tumor targeting and imaging applications, enabling the precise localization and visualization of cancerous tissues, which is essential for accurate diagnosis and treatment planning.
Used in Chemical Synthesis:
N-alpha-FMOC-Nepsilon-BOC-L-Lysine is employed as a starting material in the synthesis of various complex organic compounds, such as pentasubstituted dihydroimidazolylbutyl dihydroimidazol-3-ium salts. This is achieved through coupling with p-methylbenzhydrylamine (MBHA) resin, which allows for the formation of novel chemical entities with potential applications in various industries.
Used in Peptide Synthesis:
In the field of peptide synthesis, N-alpha-FMOC-Nepsilon-BOC-L-Lysine is used as a building block for the Fmoc-based synthesis of bis-naphthalene diimide, a threading intercalator. N-alpha-FMOC-Nepsilon-BOC-L-Lysine has potential applications in the development of new drugs and therapeutic agents, particularly in the area of nucleic acid targeting and manipulation.
Used in Analytical Chemistry:
N-alpha-FMOC-Nepsilon-BOC-L-Lysine is also used in the synthesis of ε-Boc-ε-(3,5-bis-trifluoromethyl-benzyl)-α-Fmoc-L-Lysine, which serves as a 19F NMR-based screening tool. This tool is valuable for the rapid and sensitive detection of specific molecular interactions and conformational changes, which can be crucial for understanding the mechanisms of action of new drug candidates and optimizing their design.
Check Digit Verification of cas no
The CAS Registry Mumber 71989-26-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,9,8 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 71989-26:
(7*7)+(6*1)+(5*9)+(4*8)+(3*9)+(2*2)+(1*6)=169
169 % 10 = 9
So 71989-26-9 is a valid CAS Registry Number.
InChI:InChI=1/C26H32N2O6/c1-26(2,3)34-24(31)27-15-9-8-14-22(23(29)30)28-25(32)33-16-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h4-7,10-13,21-22H,8-9,14-16H2,1-3H3,(H,27,31)(H,28,32)(H,29,30)
71989-26-9Relevant articles and documents
PROPYL CATIONIC PEPTIDE LIPIDS, SYNTHESIS METHOD THEREOF, AND APPLICATION THEREOF
-
, (2018/01/13)
A class of propyl cationic peptide lipids is propyl cationic peptide lipid compounds having a general formula structure as follows. After the propyl cationic peptide lipids are dispersed in water, a cationic liposome with a particle size of approximately 100 nm is obtained. The cationic liposome can carry plasmid DNA (pDNA) or small interfering RNA (siRNA) into cells to realize the function of gene delivery, and is almost non-toxic to the cells.
Caged xanthones: Potent inhibitors of global predominant MRSA USA300
Chaiyakunvat, Pongkorn,Anantachoke, Natthinee,Reutrakul, Vichai,Jiarpinitnun, Chutima
supporting information, p. 2980 - 2983 (2016/06/13)
Total of 22 caged xanthones were subjected to susceptibility testing of global epidemic MRSA USA300. Natural morellic acid showed the strongest potency (MIC of 12.5 μM). However, its potent toxicity diminishes MRSA therapeutic potential. We synthetically modified natural morellic acid to yield 13 derivatives (3a-3m). Synthetically modified 3b retained strong potency in MRSA growth inhibition, yet the toxicity was 20-fold less than natural morellic acid, permitting the possibility of using caged xanthones for MRSA therapeutic.
Mild oxidative cleavage of 9-BBN-protected amino acid derivatives
Ankner, Tobias,Norberg, Thomas,Kihlberg, Jan
, p. 3767 - 3770 (2015/06/16)
Protection of the amino acid moiety using 9-BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9-BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90% yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine. A representative set of 9-BBN-protected amino acid derivatives were efficiently deprotected using peracid reagents in excellent yields. Deprotection is orthogonal with several common protecting groups. Its tolerance of highly acid sensitive groups, such as trityl-protected amides and glycosidic linkages, is especially notable.
