CAS 632-20-2 D-(+)-Threonine - Catalysts / Alfa Chemistry

Synonyms

AM82240; 32T202; RTR-037350; DL-2-Amino-3-hydroxybutyric acid; D-Threonine, Vetec(TM) reagent grade, >=98%; 4-04-00-03171 (Beilstein Handbook Reference); KSC352S5H; (2R,3S)-2-amino-3-hydroxybutanoic acid; 144-98-9; AYFVYJQAPQTCCC-STHAYSLISA-N;

IUPAC Name

(2R,3S)-2-amino-3-hydroxybutanoic acid;

Molecular Weight

119.12g/mol

Molecular Formula

C4H9NO3;

Canonical SMILES

CC(C(C(=O)O)N)O;

InChI

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m0/s1;

InChI Key

AYFVYJQAPQTCCC-STHAYSLISA-N;

Storage

Store at RT.

Complexity

93.3

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

211-171-8

Exact Mass

119.058g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

119.058g/mol

Rotatable Bond Count

Topological Polar Surface Area

83.6A^2

Application

D-(+)-Threonine, the D-form isomer of the amino acid threonine, serves as an essential organic chiral source in the pharmaceutical industry. This compound plays a vital role in the asymmetric synthesis of chiral compounds and is primarily utilized in the production of chiral drugs, additives, and auxiliaries. Its unique properties make it indispensable in preparing enantiomerically pure compounds like 1,3-butanediol and as an intermediate for synthesizing chiral antibiotics. Notably, D-(+)-Threonine has been employed as a starting material in the total synthesis of protected legionaminic acid. As an optically active organic compound, it stands out for its ability to aid in producing new broad-spectrum antibiotics and serves a protective role in peptide synthesis. Additionally, D-(+)-Threonine exhibits inhibitory effects on L-threonine dehydratase and has been observed to retard growth and cell wall synthesis in Mycobacterium smegmatis. Despite its sweet and toxic nature, it holds potential applications in treating conditions like hypostatic leg ulceration.

January 27, 2025

Versatile and Essential for Chiral Synthesis

D-(+)-Threonine has been crucial in my recent laboratory work, particularly for synthesizing enantiomerically pure compounds. Its role as a chiral pool reagent is invaluable in developing antibiotics, making it indispensable for research.