N-Methyl-DL-alanine (BAT-003616)
* For research use only

Category
DL-Amino Acids
Catalog number
BAT-003616
CAS number
600-21-5
Molecular Formula
C4H9NO2
Molecular Weight
103.12
N-Methyl-DL-alanine
Synonyms
N-Me-DL-Ala-OH; 2-(methylamino)propanoic acid; L-Alanine,N-methyl; N-alpha-Methyl-DL-alanine; N-Me-DL-Ala-OH HCl; N-Methyl-DL-alanine
Appearance
White powder
Purity
≥ 98% (TLC)
Density
1.048±0.06 g/cm3
Melting Point
263-282 °C
Boiling Point
190.1±23.0 °C
Storage
Store at 2-8 °C
1.N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
Weltrowska G1, Nguyen TM, Chung NN, Wilkes BC, Schiller PW. Bioorg Med Chem Lett. 2013 Sep 15;23(18):5082-5. doi: 10.1016/j.bmcl.2013.07.036. Epub 2013 Jul 23.
Derivatives of peptides of the TIPP (Tyr-Tic-Phe-Phe; Tic=1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) family containing a guanidino (Guan) function in place of the N-terminal amino group were synthesized in an effort to improve their blood-brain barrier permeability. Unexpectedly, N-terminal amidination significantly altered the in vitro opioid activity profiles. Guan-analogues of TIPP-related δ opioid antagonists showed δ partial agonist or mixed δ partial agonist/μ partial agonist activity. Guanidinylation of the mixed μ agonist/δ antagonists H-Dmt-Tic-Phe-Phe-NH2 (DIPP-NH2) and H-Dmt-TicΨ[CH2NH]Phe-Phe-NH2 (DIPP-NH2[Ψ]) converted them to mixed μ agonist/δ agonists. A docking study revealed distinct positioning of DIPP-NH2 and Guan-DIPP-NH2 in the δ receptor binding site. Lys(3)-analogues of DIPP-NH2 and DIPP-NH2[Ψ] (guanidinylated or non-guanidinylated) turned out to be mixed μ/κ agonists with δ antagonist-, δ partial agonist- or δ full agonist activity.
2.Two phase 3 trials of bapineuzumab in mild-to-moderate Alzheimer's disease.
Salloway S, Sperling R, Fox NC, Blennow K, Klunk W, Raskind M, Sabbagh M, Honig LS, Porsteinsson AP, Ferris S, Reichert M, Ketter N, Nejadnik B, Guenzler V, Miloslavsky M, Wang D, Lu Y, Lull J, Tudor IC, Liu E, Grundman M, Yuen E, Black R, Brashear HR; Bapineuzumab 301 and 302 Clinical Trial Investigators. N Engl J Med. 2014 Jan 23;370(4):322-33. doi: 10.1056/NEJMoa1304839.
BACKGROUND: Bapineuzumab, a humanized anti-amyloid-beta monoclonal antibody, is in clinical development for the treatment of Alzheimer's disease.
3.Novel monodisperse PEGtide dendrons: design, fabrication, and evaluation of mannose receptor-mediated macrophage targeting.
Gao J, Chen P, Singh Y, Zhang X, Szekely Z, Stein S, Sinko PJ. Bioconjug Chem. 2013 Aug 21;24(8):1332-44.
Novel PEGtide dendrons of generations 1 through 5 (G1.0–5.0) containing alternating discrete poly(ethylene glycol) (dPEG) and amino acid/peptide moieties were designed and developed. To demonstrate their targeting utility as nanocarriers, PEGtide dendrons functionalized with mannose residues were developed and evaluated for macrophage targeting. PEGtide dendrons were synthesized using 9-fluorenylmethyloxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) protocols. The N-α-Fmoc-N-ε-(5-carboxyfluorescein)-l-lysine (Fmoc-Lys(5-FAM)-OH) and monodisperse Fmoc-dPEG6-OH were sequentially coupled to Fmoc-β-Ala-resin to obtain the resin-bound intermediate Fmoc-dPEG6-Lys(5-FAM)-β-Ala (1). G1.0 dendrons were obtained by sequentially coupling Fmoc-Lys(Fmoc)-OH, Fmoc-β-Ala-OH, and Fmoc-dPEG6-OH to 1. Dendrons of higher generation, G2.0–5.0, were obtained by repeating the coupling cycles used for the synthesis of G1.0. Dendrons containing eight mannose residues (G3.
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