87768-65-8

Upstream product

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

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 academic research and scientific papers

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.

Capped diaminopropionamide-glycine dipeptides are inhibitors of CC chemokine receptor 2 (CCR2)

A new series of CCR2 antagonists has been discovered that incorporates intramolecular hydrogen bonding as a strategy for rigidifying the scaffold. The structure-activity relationship was established through initial systematic modification of substitution pattern and chain length, followed by independent optimization of three different substituents (benzylamine, carboxamide, and benzamide). Several of the acyclic compounds display 10-30 nM binding affinity for CCR2. Moreover, these antagonists are able to block both MCP-1-induced Ca2+ flux and monocyte chemotaxis, and are selective for binding to CCR2 over CCR1 and CCR3.

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.

RGD mimetics containing a central hydantoin scaffold: α(v)β3 vs α(IIb)β3 selectivity requirements

The synthesis of a series of RGD mimetic α(v)β3 antagonists containing a hydantoin scaffold is shown. The results demonstrate some of the structural requirements for the design of selective α(v)β3 antagonists (vs α(IIb)β3)

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.