Z-L-methionine
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Z-L-methionine

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Category
CBZ-Amino Acids
Catalog number
BAT-003362
CAS number
1152-62-1
Molecular Formula
C13H17NO4S
Molecular Weight
283.40
Z-L-methionine
IUPAC Name
(2S)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-L-Met-OH; N-[(Benzyloxy)Carbonyl]-L-Methionine
Appearance
White to off-white crystalline powder
Purity
≥ 99% (assay)
Density
1.253 g/cm3
Melting Point
67-71 °C
Boiling Point
504.7°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H17NO4S/c1-19-8-7-11(12(15)16)14-13(17)18-9-10-5-3-2-4-6-10/h2-6,11H,7-9H2,1H3,(H,14,17)(H,15,16)/t11-/m0/s1
InChI Key
FPKHNNQXKZMOJJ-NSHDSACASA-N
Canonical SMILES
CSCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
1. Bioavailability of D-methionine relative to L-methionine for nursery pigs using the slope-ratio assay
Changsu Kong, Jong Young Ahn, Beob G Kim PeerJ. 2016 Sep 7;4:e2368. doi: 10.7717/peerj.2368. eCollection 2016.
This experiment was conducted to determine the bioavailability of D-methionine (Met) relative to L-Met for nursery pigs using the slope-ratio assay. A total of 50 crossbred barrows with an initial BW of 13.5 kg (SD = 1.0) were used in an N balance study. A Met-deficient basal diet (BD) was formulated to contain an adequate amount of all amino acids (AA) for 10-20 kg pigs except for Met. The two reference diets were prepared by supplementing the BD with 0.4 or 0.8 g L-Met/kg at the expense of corn starch, and an equivalent concentration of D-Met was added to the BD for the two test diets. The pigs were adapted to the experimental diets for 5 d and then total but separated collection of feces and urine was conducted for 4 d according to the marker-to-marker procedure. Nitrogen intakes were similar across the treatments. Fecal N output was not affected by Met supplementation regardless of source and consequently apparent N digestibility did not change. Conversely, there was a negative linear response (P < 0.01) to Met supplementation with both Met isomers in urinary N output, which resulted in increased retained N (g/4 d) and N retention (% of intake). No quadratic response was observed in any of the N balance criteria. The estimated bioavailability of D-Met relative to L-Met from urinary N output (g/4 d) and N retention (% of intake) as dependent variables using supplemental Met intake (g/4 d) as an independent variable were 87.6% and 89.6%, respectively; however, approximately 95% of the fiducial limits for the relative bioavailability estimates included 100%. In conclusion, with an absence of statistical significance, the present study indicated that the mean relative bioequivalence of D- to L-Met was 87.6% based on urinary N output or 89.6% based on N retention.
2. Effects of supplemental d-methionine in comparison to l-methionine on nitrogen retention, gut morphology, antioxidant status, and mRNA abundance of amino acid transporters in weanling pigs
Charmaine D Espinosa, John K Mathai, Laia Blavi, Yanhong Liu, John K Htoo, J Caroline Gonzalez-Vega, Hans H Stein J Anim Sci. 2021 Sep 1;99(9):skab248. doi: 10.1093/jas/skab248.
An N-balance experiment was conducted to test the hypothesis that d-Methionine (d-Met) has the same bioavailability and efficacy as l-Methionine (l-Met) when fed to weanling pigs. A Met-deficient basal diet containing 0.24% standardized ileal digestible (SID) Met was formulated. Six additional diets were formulated by adding 0.036%, 0.072%, or 0.108% d-Met or l-Met to the basal diet, and these diets, therefore, contained 77%, 87%, or 97% of the requirement for SID Met. Fifty-six barrows (10.53 ± 1.17 kg) were housed in metabolism crates and allotted to the seven diets with eight replicate pigs per diet. Feces and urine were collected quantitatively with 7-d adaptation and 5-d collection periods. Blood and tissue samples from pigs fed the basal diet and pigs fed diets containing 0.108% supplemental Met were collected on the last day. Results indicated that N retention (%) linearly increased (P < 0.01) as supplemental d-Met or l-Met increased in diets. Based on N retention (%) as a response, the linear slope-ratio regression estimated the bioavailability of d-Met relative to l-Met to be 101% (95% confidence interval: 57%-146%). The villus height and crypt depth in the jejunum were not affected by the Met level or Met source. Total antioxidant capacity or thiobarbituric acid reactive substance concentrations in plasma or tissue samples from pigs fed the control diet or diets containing 0.108% supplemental d-Met or l-Met were not different. Abundance of mRNA for some AA transporters analyzed in intestinal mucosa of pigs also did not differ. Therefore, it is concluded that d-Met and l-Met are equally bioavailable for weanling pigs.
3. Development of New D,L-Methionine-based Gelators
Shunichi Suga, Masahiro Suzuki, Kenji Hanabusa J Oleo Sci. 2018;67(5):539-549. doi: 10.5650/jos.ess17248.
D,L-Methionine was chosen as a starting material for the preparation of a new gelator N-10-undecenoyl-D,L-methionylaminooctadecane (DL-Met-R18). Three oligo (dimethylsiloxane)-containing gelators, DL-Met-R18/Si3, DL-Met-R18/Si7-8, and DL-Met-R18/Si14-15, were also prepared from DL-Met-R18 by hydrosilylation reactions. Their gelation abilities were evaluated on the basis of the minimum gel concentration using nine solvents. Compound DL-Met-R18 was able to gelate liquid paraffin and silicone oil, but it crystallized in most solvents. However, DL-Met-R18/Si7-8 resulted to be the best gelator, gelling eight solvents at low concentrations. The results of gelation tests demonstrated that the ability to form stable gels decreases in the following order: DL-Met-R18/Si7-8 ≈ DL-Met-R18/Si14-15 > DL-Met-R18/Si3 >> DL-Met-R18. The aspects and thermal stabilities of the gels were investigated using three-component mixtures of solvents composed of hexadecyl 2-ethylhexanoate, liquid paraffin, and decamethylcyclopentasiloxane (66 combinations). DL-Met-R18/Si3, DL-Met-R18/Si7-8, and DL-Met-R18/Si14-15 could form gels with all these mixed solvent combinations; particularly, DL-Met-R18/Si7-8 gave rise to transparent or translucent gels. FT-IR spectra suggested that the formation of hydrogen bonds between the NH and C=O groups of the amides is one of driving forces involved in the gelation process. Aggregates comprising three-dimensional networks were studied by transmission electron microscopy. Moreover, the viscoelastic behavior of the gels was investigated by rheology measurements.
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