2-Methyl-D-proline - CAS 63399-77-9

2-Methyl-D-proline, a unique non-proteinogenic amino acid, displays promising antiviral capabilities. Extensively researched for its therapeutic potential in combating viral infections, particularly when utilized concomitantly with various antiviral agents.

Catalog Number

63399-77-9

CAS

63399-77-9

IUPAC Name

(2R)-2-methylpyrrolidine-2-carboxylic acid

Synonyms

D-Proline, 2-methyl-; (+)-2-Methyl-D-proline; (R)-2-Methylproline; (R)-2-Methylpyrrolidine-2-carboxylic acid; α-Methyl-D-proline; H-α-ME-D-PRO-OH

Molecular Weight

129.16

Molecular Formula

C6H11NO2

Product Information

Canonical SMILES

CC1(CCCN1)C(=O)O

InChI

InChI=1S/C6H11NO2/c1-6(5(8)9)3-2-4-7-6/h7H,2-4H2,1H3,(H,8,9)/t6-/m1/s1

InChI Key

LWHHAVWYGIBIEU-ZCFIWIBFSA-N

Purity

95%

Appearance

White Solid

Storage

Store at 2-8°C

Boiling Point

241.9±33.0°C at 760 mmHg

Melting Point

340°C (dec.)

Density

1.119±0.06 g/cm3

Reference Reading

1.Identification of ligand binding regions of the Saccharomyces cerevisiae alpha-factor pheromone receptor by photoaffinity cross-linking.

Son CD1, Sargsyan H, Naider F, Becker JM. Biochemistry. 2004 Oct 19;43(41):13193-203.

Analogues of alpha-factor, Saccharomyces cerevisiae tridecapeptide mating pheromone (H-Trp-His-Trp-Leu-Gln-Leu-Lys-Pro-Gly-Gln-Pro-Met-Tyr-OH), containing p-benzoylphenylalanine (Bpa), a photoactivatable group, and biotin as a tag, were synthesized using solid-phase methodologies on a p-benzyloxybenzyl alcohol polystyrene resin. Bpa was inserted at positions 1, 3, 5, 8, and 13 of alpha-factor to generate a set of cross-linkable analogues spanning the pheromone. The biological activity (growth arrest assay) and binding affinities of all analogues for the alpha-factor receptor (Ste2p) were determined. Two of the analogues that were tested, Bpa(1) and Bpa(5), showed 3-4-fold lower affinity than the alpha-factor, whereas Bpa(3) and Bpa(13) had 7-12-fold lower affinities. Bpa(8) competed poorly with [(3)H]-alpha-factor for Ste2p. All of the analogues tested except Bpa(8) had detectable halos in the growth arrest assay, indicating that these analogues are alpha-factor agonists.

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