L-Lysine Dihydrochloride
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L-Lysine Dihydrochloride

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Category
L-Amino Acids
Catalog number
BAT-004726
CAS number
657-26-1
Molecular Formula
C6H16Cl2N2O2
Molecular Weight
219.11
L-Lysine Dihydrochloride
IUPAC Name
(2S)-2,6-diaminohexanoic acid;dihydrochloride
Appearance
White to very light yellow Crystalline Powder
Melting Point
200-206 °C(lit.)
InChI
InChI=1S/C6H14N2O2.2ClH/c7-4-2-1-3-5(8)6(9)10;;/h5H,1-4,7-8H2,(H,9,10);2*1H/t5-;;/m0../s1
InChI Key
JBBURJFZIMRPCZ-XRIGFGBMSA-N
Canonical SMILES
C(CCN)CC(C(=O)O)N.Cl.Cl
1. Bioefficacy of L-lysine sulfate compared with feed-grade L-lysine-HCl in young pigs
M R Smiricky-Tjardes, I Mavromichalis, D M Albin, J E Wubben, M Rademacher, V M Gabert J Anim Sci. 2004 Sep;82(9):2610-4. doi: 10.2527/2004.8292610x.
A pig growth assay was conducted to determine the relative biological value (RBV) of lysine from L-lysine sulfate compared with feed-grade L-lysine HCl. One hundred nursery pigs with an average initial BW of 9.5 +/- 1.5 kg were blocked by BW and gender and allotted randomly to five dietary treatments in five replicates of four pigs per pen. A corn-peanut meal diet containing 0.6% total lysine (as-fed basis) was supplemented with two levels (0.1 and 0.2%) of lysine from L-lysine-HCl or L-lysine sulfate. The RBV of L-lysine sulfate was determined using multiple regression slope-ratio methodology, with ADG and G:F as the response criteria. At the tested levels, linear responses for gain and G:F were obtained from increments of lysine from the two lysine sources. When ADG was regressed on supplemental lysine intake, the RBV of lysine in L-lysine sulfate was 99% of the RBV of lysine in L-lysine HCl. When G:F was regressed on supplemental lysine intake, the RBV of lysine in L-lysine sulfate was 97% of the RBV of lysine in L-lysine-HCl. The t-test analysis revealed that the RBV of lysine in L-lysine sulfate was not significantly different from the RBV of lysine in L-lysine HCl, which was assumed to be 100% bioavailable. In conclusion, L-lysine sulfate can replace L-lysine HCl in diets for growing swine.
2. Relative bioavailability of l-lysine sulfate is equivalent to that of l-lysine HCl for nursery piglets
Jorge Y P Palencia, et al. J Anim Sci. 2019 Jan 1;97(1):269-278. doi: 10.1093/jas/sky394.
Supplementary l-lysine sources include l-lysine HCl and l-lysine sulfate. l-Lysine sulfate contains at least 50% l-Lys and other components as residues from the fermentation process, other amino acids, and other organic and inorganic substances, being an alternative to l-Lys HCl. The aim of this study was to evaluate the relative bioavailability (RBV) of l-Lys sulfate in comparison with l-Lys HCl and its effects on performance, blood parameters, intestinal functionality, and the apparent total tract digestibility in nursery piglets. A total of 168 female piglets (DB90 × PIC337), weaned at 22 d (BW = 6.29 ± 0.41 kg), were distributed in seven dietary treatments and eight replicates, with three pigs per pen. The experimental period of 42 d was divided into two phases (phase 1, days 0-21; phase 2, days 21 to 42). The basal diet (CON) was lysine-deficient formulated to meet 73% of standardized ileal digestible Lys requirements. For the other diets, the CON was supplemented with three levels (80%, 90%, and 100% of standardized ileal digestible Lys requirements) of l-Lys sulfate (70% l-Lys) or l-Lys HCl (79% l-Lys). There were no significant differences (P > 0.05) in the performance and concentrations of plasma urea and creatinine between the l-Lys sources. The RBV of l-Lys sulfate relative to l-Lys HCl was 106%, 119%, and 117% for effects on ADG, G:F, and plasma urea, respectively. Lys deficiency resulted in a greater (P < 0.05) incidence of diarrhea, while pigs supplemented with Lys sulfate or Lys HCl showed greater (P < 0.05) villus height in the jejunum when compared to those receiving the CON. Diets supplemented with l-Lys sulfate had greater (P < 0.05) apparent total tract digestibility of dry matter, gross energy, and crude protein. In conclusion, the RBV of l-Lys sulfate for effects on ADG, G:F, and plasma urea is equivalent to that of l-Lys HCl for nursery piglets.
3. Characterization of an L-α,β-diaminopropionic acid polymer with comb-like structure isolated from a poly(ε-L-lysine)-producing Streptomyces sp
Munenori Takehara, Masayuki Saimura, Haruka Inaba, Yoshinao Kato, Shogo Muro, Tatsuki Matsunaga, Kazuya Yamanaka Appl Microbiol Biotechnol. 2021 Apr;105(8):3145-3157. doi: 10.1007/s00253-021-11257-3. Epub 2021 Apr 12.
Polymers of basic amino acids function as polycationic compounds under physiological conditions and exhibit intriguing biological properties, such as antimicrobial and antiviral activities, immunopotentiating ability, and DNA-binding activity. Poly(ε-L-lysine) (ε-PL) produced by some strains of Streptomyces spp. is a cationic homopolymer of L-lysine linking between ε-amino and α-carboxylic acid functional groups and has been used as a food preservative based on its biocompatibility and biodegradability. An ε-PL-producing strain of Streptomyces sp. USE-33 was found to secrete a novel polycationic substance into its culture broth along with ε-PL. High-performance liquid chromatography analyses and one- and two-dimensional 1H and 13C nuclear magnetic resonance (NMR) experiments, accompanied by NMR titration studies, revealed that the secreted substance was poly[β-(L-diaminopropionyl-L-diaminopropionic acid)], PAP, characterized by an isopeptide backbone linking between the β-amino and α-carboxylic acid groups of L-α,β-diaminopropionic acid (L-Dpr) with pendent L-Dpr residues. PAP had a molecular weight of 500 to 1400, and copolymers composed of the two amino acids L-Dpr and L-lysine were not detected in the producer strain USE-33. The strain coproduced high levels of the two poly(amino acid)s in the presence of glycerol, citrate, and ammonium sulfate at pH 4.0 in a two-stage cultivation procedure. PAP exhibited strong inhibitory activities against several yeasts and weaker activities against bacteria than ε-PL. PAP may share a number of biological functions with ε-PL, and the use of PAP along with ε-PL has potential as a specific and advanced material for technical applications in various fields.Key points· Novel cationic poly(amino acid) was found in an ε-PL-producing Streptomyces species.· The l-α,β-diaminopropionic acid polymer was characterized by a comb-like structure.· The novel poly(amino acid), PAP, exhibited antibacterial and antifungal activities.
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