87768-65-8

Basic information

• Product Name: N-β-Z-L-diaminopropionic acid methyl ester
• Synonyms: N-β-Z-L-diaminopropionic acid methyl ester
• CAS NO: 87768-65-8
• Molecular Weight: 252.27
• Mol File: 87768-65-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-β-Z-L-diaminopropionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-β-Z-L-diaminopropionic acid methyl ester(87768-65-8)
• EPA Substance Registry System: N-β-Z-L-diaminopropionic acid methyl ester(87768-65-8)

Safety Data

• Hazardous Substances Data: 87768-65-8(Hazardous Substances Data)

Upstream product

• 61040-22-0 N^β-benzyloxycarbonyl-N^α-Boc-(S)-β-aminoalanine methyl ester 
• 67-56-1 methanol 
• 659747-11-2 C₁₅H₂₄N₂O₇ 
• 659747-12-3 C₂₂H₃₂N₂O₈ 
• 176755-21-8 N-bis-(tert-butoxycarbonyl)aspartic acid α-methyl ester 
• 100-51-6 benzyl alcohol 
• 28415-54-5 N^β-(benzyloxycarbonyl)-L-α,β-diaminopropionic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 61040-22-0 N^β-benzyloxycarbonyl-N^α-Boc-(S)-β-aminoalanine methyl ester 
• 176755-22-9 (S)-1-((S)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-propionyl)-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 176755-23-0 (S)-1-((S)-2-Acetylamino-3-benzyloxycarbonylamino-propionyl)-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 

Relevant articles and documents

Synthesis and evaluation of dihydroimidazolo and dihydrooxazolo ring-fused 2-pyridones-targeting pilus biogenesis in uropathogenic bacteria

Dihydrothiazolo ring-fused 2-pyridones have previously been shown to inhibit pilus assembly in uropathogenic Escherichia coli. Methods have now been developed to synthesize both dihydroimidazolo and dihydrooxazolo ring-fused 2-pyridones. To obtain the nitrogen analogs, Cbz-protected imidazolines were reacted with an acyl-Meldrum's acid derivative under acidic conditions. To prepare the oxygen analogs, a one-pot procedure was developed that allowed synthesis of dihydrooxazolo ring-fused 2-pyridones starting from acylated serine derivatives. After hydrolysis to their corresponding carboxylic acids and lithium carboxylates, biological evaluation revealed that the sulfur could be replaced by an oxygen atom and still maintains the ability to inhibit pilus assembly in uropathogenic E. coli. However, introducing a secondary amine instead of oxygen resulted in a substantial decrease in biological activity.

An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

(Matrix presented) An efficient and cost-effective synthesis of N(α)-Boc2-N(β)-Cbz-2,3-diaminopropionic acid is reported. The synthesis starts from commercially available N(α)-Boc-Asp(OBn)-OH and employs a Curtius rearrangement to establish the β-nitrogen. Proper protection of the α-nitrogen is essential for the success of the Curtius rearrangement.

A new synthesis of cyclotheonamide B via guanidination of ornithine

A macrocyclic thrombin inhibitor, cyclotheonamide B (1, R = Ac) was synthesized via a new approach: guanidination of the ornithine-containing macrocyclic peptide (2). In comparison of various coupling reagents, pentafluorophenyl diphenylphosphinate (FDPP) gave the macrocyclic peptide (2) in good yield, and the configuration of the amino acid residue has been revealed to be important for the macrolactamization.