105449-18-1

Basic information

• Product Name: Butanoic acid, 4-[[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]amino]-, phenylmethyl ester
• CAS NO: 105449-18-1
• Molecular Formula: C19H28N2O5
• Molecular Weight: 364.442
• Mol File: 105449-18-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 4-[[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]amino]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-[[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]amino]-, phenylmethyl ester(105449-18-1)
• EPA Substance Registry System: Butanoic acid, 4-[[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxopropyl]amino]-, phenylmethyl ester(105449-18-1)

Safety Data

• Hazardous Substances Data: 105449-18-1(Hazardous Substances Data)

Upstream product

• 15761-38-3 L-N-Boc-Ala 
• 46347-99-3 benzyl 4-aminobutanoate 
• 78287-52-2 4-aminobutanoic acid benzyl ester hydrochloride 
• 95656-84-1 benzyl 4-((tert-butoxycarbonyl)amino)butanoate 
• 100-39-0 benzyl bromide 
• 26727-22-0 4-(benzyloxy)-4-oxobutan-1-aminium 4-methylbenzenesulfonate 

Relevant articles and documents

Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross-Linking Activity of a Transpeptidase of l,d Specificity

The carbapenem class of β-lactams has been optimized against Gram-negative bacteria producing extended-spectrum β-lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d-transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation of these unusual targets is sought herein by exploiting the nucleophilicity of the C8 hydroxyl group to introduce chemical diversity. As β-lactams are structure analogs of peptidoglycan precursors, the substituents were chosen to increase similarity between the drug and the substrate. Fourteen peptido-carbapenems were efficiently synthesized. They were more effective than the reference drug, meropenem, owing to the positive impact of a phenethylthio substituent introduced at position C2 but the peptidomimetics added at position C8 did not further improve the activity. Thus, position C8 can be modified to modulate the pharmacokinetic properties of highly efficient carbapenems.

Synthesis and evaluation of new elastase substrates as tripartate prodrugs

Compounds consisting of a peptide sequence, 4-aminobutyric acid or 5-aminovaleric acid, respectively, as spacer units, and benzyl alcohol as a model leaving group have been prepared and tested for their ability to serve as substrates for porcine pancreatic elastase and human polymorphnuclear elastase. Those compounds containing an Ala-Ala-Ala sequence served as effective substrates for both enzymes. Hydrolytic cleavage, however, occurred exclusively at the ester bond, not at the peptide-spacer bond. In order to direct the cleavage site from the ester to the amide bond the peptide sequence was varied. We introduced a proline residue in P3 (in relation to the ester bond) which is known to prevent the cleavage of a substrate by elastase. No hydrolysis, however, either of the ester bond or of the peptide-spacer bond, was found for these compounds.