O-Methyl-L-threonine (BAT-004172)
* For research use only

Category
L-Amino Acids
Catalog number
BAT-004172
CAS number
4144-02-9
Molecular Formula
C5H11NO3
Molecular Weight
133.15
O-Methyl-L-threonine
Synonyms
L-Thr(Me)-OH; (S)-2-Amino-3-methoxybutanoic acid; (2S,3R)-2-Amino-3-Methoxybutanoic Acid
Appearance
White to off-white crystalline powder
Purity
≥ 98.5% (TLC)
Density
1.143±0.06 g/cm3(Predicted)
Melting Point
203-220 ºC
Boiling Point
248.0±30.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C5H11NO3/c1-3(9-2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t3-,4+/m1/s1
InChI Key
FYCWLJLGIAUCCL-DMTCNVIQSA-N
Canonical SMILES
CC(C(C(=O)O)N)OC
1.Amino acids and peptides. XXX. Synthesis of eglin c (41-49) and eglin c (60-63) and examination of their inhibitory activity towards human leukocyte elastase, cathepsin G, porcine pancreatic elastase and alpha-chymotrypsin.
Tsuboi S1, Takeda M, Okada Y, Nagamatsu Y, Yamamoto J. Chem Pharm Bull (Tokyo). 1991 Jan;39(1):184-6.
H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OH and H-Thr-Asn-Val-Val-OH, which correspond to the sequences 41-49 and 60-63 of eglin c, respectively, were synthesized by a conventional solution approach using the newly developed 6-chloro-2-pyridyl ester method. The inhibitory activities of the above two peptides against human leukocyte elastase, cathepsin G, porcine pancreatic elastase and alpha-chymotrypsin were examined in comparison with those of the corresponding methyl esters.
2.Design, synthesis and biological evaluation of a new bridged immunosuppressor.
Szewczuk Z1, Wilczyński A, Petry I, Siemion IZ, Wieczorek Z. Acta Biochim Pol. 2001;48(4):1147-50.
A bridged peptide with the sequence: H-Thr-Pro-Gln-Arg-Gly-Asp-Val-gamma-Abu-Asn-Asp-Gln-Glu-Glu-Thr-Thr-Gly-Val-Val-Ser-Thr-Pro-Leu-Ile-Arg-Asn-Gly-OH was designed to mimic the discontinuous epitope of the HLA-DQ molecule that might interact with CD4. The bridged peptide revealed distinct suppressory effect in the humoral immune response. This result supports our suggestion that the 164-172 region of the HLA-DQ molecule may enhance its interactions with coreceptors, possibly with CD4.
3.Design, synthesis, and testing of potential antisickling agents. 9. Cyclic tetrapeptide homologs as mimics of the mutation site of hemoglobin S.
Sheh L, Mokotoff M, Abraham DJ. Int J Pept Protein Res. 1987 Apr;29(4):509-20.
As part of our continuing search for new agents which might be useful for the treatment of sickle-cell anemia, we have synthesized two cyclic tetrapeptide homologs, cyclo(-Val-Glu[-Thr-Pro-]-OH) (1a) and cyclo(-Phe-Glu[-Thr-Pro-]-OH (1b), and a tetrapeptide lactone homolog cyclo(H-Thr-Pro-Val-Glu-OH) (2). The intent was that these peptides would mimic a tetrapeptide region around the mutation site of HbS and thus be able to bind at the acceptor site of HbS and thereby inhibit polymerization. The synthesis of the linear peptides was accomplished in solution using both the polymeric reagent (PHBT) and DCC/HOBT methods; cyclization was accomplished by an improved method. 13C-n.m.r. studies were performed which allowed us to assign the conformation about the Thr-Pro bond in 1a and 2 as trans. The cyclic peptides were tested for their ability to increase the solubility of HbS under deoxygenating conditions, but only 1a had any antigelling activity, albeit low.
4.Structure-activity relationships of peptide T-related pentapeptides.
Marastoni M1, Salvadori S, Balboni G, Spisani S, Gavioli R, Traniello S, Tomatis R. Arzneimittelforschung. 1989 Aug;39(8):926-8.
Fifteen pentapeptide analogs of C-terminal fragment of peptide T, H-Ala-Ser-Thr-Thr-Thr-Asn-Tyr-Thr-OH, were prepared and tested for human monocyte chemotaxis. Structure-activity studies suggest that the potent chemotactic activity of H-Thr-Thr-Asn-Tyr-Thr-OH is mediated through the polar properties of the C-terminal carboxyl group and Thr side chains at the critical positions 5 and 8, while the hydroxyl group of N-terminal Thr and its free amino function are not essential requirements for CD4 receptor interactions.
Bio Calculators
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L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
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