L-Lysinamide

L-Lysinamide

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Category Others
Catalog number BBF-04749
CAS 32388-19-5
Molecular Weight 145.21
Molecular Formula C6H15N3O

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Specification

Synonyms Lysine amide; Hexanamide, 2,6-diamino-, (2S)-; lysinamide
IUPAC Name (2S)-2,6-diaminohexanamide
Canonical SMILES C(CCN)CC(C(=O)N)N
InChI InChI=1S/C6H15N3O/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H2,9,10)/t5-/m0/s1
InChI Key HKXLAGBDJVHRQG-YFKPBYRVSA-N

Reference Reading

1. Milk Metabolomics Reveals Potential Biomarkers for Early Prediction of Pregnancy in Buffaloes Having Undergone Artificial Insemination
Donato de Nicola, Francesco Vinale, Angela Salzano, Giada d'Errico, Anastasia Vassetti, Nunzia D'Onofrio, Maria Luisa Balestrieri, Gianluca Neglia Animals (Basel). 2020 Apr 27;10(5):758. doi: 10.3390/ani10050758.
This study aimed to identify potential biomarkers for early pregnancy diagnosis in buffaloes subjected to artificial insemination (AI). The study was carried out on 10 pregnant and 10 non-pregnant buffaloes that were synchronized by Ovsynch-Timed Artificial Insemination Program and have undergone the first AI. Furthermore, milk samples were individually collected ten days before AI (the start of the synchronization treatment), on the day of AI, day 7 and 18 after AI, and were analyzed by LC-MS. Statistical analysis was carried out by using Mass Profile Professional (Agilent Technologies, Santa Clara, CA, USA). Metabolomic analysis revealed the presence of several metabolites differentially expressed between pregnant and non-pregnant buffaloes. Among these, a total of five metabolites were identified by comparison with an online database and a standard compound as acetylcarnitine (3-Acetoxy-4-(trimethylammonio)butanoate), arginine-succinic acid hydrate, 5'-O-{[3-({4-[(3aminopropyl)amino]butyl}amino)propyl]carbamoyl}-2'-deoxyadenosine, N-(1-Hydroxy-2-hexadecanyl)pentadecanamide, and N-[2,3-Bis(dodecyloxy)propyl]-L-lysinamide). Interestingly, acetylcarnitine was dominant in milk samples collected from non-pregnant buffaloes. The results obtained from milk metabolic profile and hierarchical clustering analysis revealed significant differences between pregnant and non-pregnant buffaloes, as well as in the metabolite expression. Overall, the findings indicate the potential of milk metabolomics as a powerful tool to identify biomarkers of early pregnancy in buffalo undergoing AI.
2. Divergence in noncognate amino acid recognition between class I and class II lysyl-tRNA synthetases
Jeffrey Levengood, Sandro F Ataide, Hervé Roy, Michael Ibba J Biol Chem. 2004 Apr 23;279(17):17707-14. doi: 10.1074/jbc.M313665200. Epub 2004 Jan 27.
Lysine insertion during coded protein synthesis requires lysyl-tRNA(Lys), which is synthesized by lysyl-tRNA synthetase (LysRS). Two unrelated forms of LysRS are known: LysRS2, which is found in eukaryotes, most bacteria, and a few archaea, and LysRS1, which is found in most archaea and a few bacteria. To compare amino acid recognition between the two forms of LysRS, the effects of l-lysine analogues on aminoacylation were investigated. Both enzymes showed stereospecificity toward the l-enantiomer of lysine and discriminated against noncognate amino acids with different R-groups (arginine, ornithine). Lysine analogues containing substitutions at other positions were generally most effective as inhibitors of LysRS2. For example, the K(i) values for aminoacylation of S-(2-aminoethyl)-l-cysteine and l-lysinamide were over 180-fold lower with LysRS2 than with LysRS1. Of the other analogues tested, only gamma-aminobutyric acid showed a significantly higher K(i) for LysRS2 than LysRS1. These data indicate that the lysine-binding site is more open in LysRS2 than in LysRS1, in agreement with previous structural studies. The physiological significance of divergent amino acid recognition was reflected by the in vivo resistance to growth inhibition imparted by LysRS1 against S-(2-aminoethyl)-l-cysteine and LysRS2 against gamma-aminobutyric acid. These differences in resistance to naturally occurring noncognate amino acids suggest the distribution of LysRS1 and LysRS2 contributes to quality control during protein synthesis. In addition, the specific inhibition of LysRS1 indicates it is a potential drug target.
3. Synthesis and Characterization of New Optically Active Poly (ethyl L-lysinamide)s and Poly (ethyl L-lysinimide)s
Saeed Zahmatkesh, Mohammad Reza Vakili J Amino Acids. 2010;2010:910906. doi: 10.4061/2010/910906. Epub 2010 Jul 13.
Ethyl L-lysine dihydrochloride was reacted with three different dianhydrides to yield the poly (ethyl L-lysinimide)s (PI(1-3)); it was also reacted with two different diacyl chlorides to yield the poly (ethyl L-lysinamide)s (PA(4-5)). The resulting polymers have inherent viscosities in the range of 0.15 to 0.42 dL g(-1). These polymers are prepared from an inexpensive starting material and are optically active, potentially ion exchangeable, semicrystalline, thermally stable, and soluble in polar aprotic solvents such as DMF, DMSO, NMP, DMAc, and sulfuric acid. All of the above polymers were fully characterized by FT-IR and (1)H NMR spectroscopy, elemental analysis, WAX diffraction, TGA, inherent viscosity measurement, and specific rotation.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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