CAS 49841-95-4

(2S,5R,6S)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description:

The chemical substance with the name "(2S,5R,6S)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid" and CAS number "49841-95-4" is known as a beta-lactam antibiotic, specifically a derivative of thienamycin. It exhibits a bicyclic structure that includes a thiazolidine ring, contributing to its biological activity. This compound is characterized by its ability to inhibit bacterial cell wall synthesis, making it effective against a range of Gram-positive and Gram-negative bacteria. The presence of the amino and carboxylic acid functional groups enhances its solubility and reactivity, while the dimethyl and phenylacetyl substituents influence its pharmacokinetic properties. Its stereochemistry, indicated by the specific configuration at multiple chiral centers, is crucial for its biological activity and interaction with bacterial enzymes. Overall, this compound represents a significant class of antibiotics with potential therapeutic applications in treating bacterial infections.

Formula: C₁₆H₁₉N₃O₄S

InChI: InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10+,11+,14-/m1/s1

InChI key: InChIKey=AVKUERGKIZMTKX-YAMSLAJTSA-N

SMILES: C(O)(=O)[C@@H]1N2[C@@]([C@@H](NC([C@H](N)C3=CC=CC=C3)=O)C2=O)(SC1(C)C)[H]

Synonyms:

• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6S)-
• (2S,5R,6S)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 6-Epiampicillin
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2α,5α,6α(S*)]]-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6S)-

6-epi-Ampicillin

Controlled Product

CAS: 49841-95-4

Formula: C₁₆H₁₉N₃O₄S

Color and Shape: Neat

Molecular weight: 385.0863

Ref: TR-A634555