117156-31-7

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 15100-75-1 L-phenylalanine tert-butyl ester hydrochloride 
• 75-44-5 phosgene 

Downstream Products

• 1416343-02-6 N-(N-fluorenylidene-2-aza-glycinyl)-L-phenylalanine tert-butyl ester 
• 1416343-04-8 N-(N-fluorenylidene-2-aza-2-propargylglycinyl)-L-phenylalanine tert-butyl ester 
• 1432474-23-1 C₃₆H₃₇NO₁₅ 
• 1432474-28-6 C₃₂H₂₉NO₁₅ 

Relevant academic research and scientific papers

Conjugates of Tetramethylpyrazine’ metabolites and amino acid as potential antiplatelet agents

Tetramethylpyrazine (TMP) is commonly used as an antiplatelet drug in clinic. However, the short half-life and low bioavailability limited its applications. 3, 5, 6-Trimethylpyrazine-2-carboxAylic acid (TMP-COOH) and 2-hydroxy-3, 5, 6-trimethylpyrazine (T

Enzymatic Cβ-H Functionalization of l -Arg and l -Leu in Nonribosomally Derived Peptidyl Natural Products: A Tale of Two Oxidoreductases

Muraymycins are peptidyl nucleoside antibiotics that contain two Cβ-modified amino acids, (2S,3S)-capreomycidine and (2S,3S)-β-OH-Leu. The former is also a component of chymostatins, which are aldehyde-containing peptidic protease inhibitors that-like muraymycin-are derived from nonribosomal peptide synthetases (NRPSs). Using feeding experiments and in vitro characterization of 12 recombinant proteins, the biosynthetic mechanism for both nonproteinogenic amino acids is now defined. The formation of (2S,3S)-capreomycidine is shown to involve an FAD-dependent dehydrogenase:cyclase that requires an NRPS-bound pathway intermediate as a substrate. This cryptic dehydrogenation strategy is both temporally and mechanistically distinct in comparison to the biosynthesis of other capreomycidine diastereomers, which has previously been shown to proceed by Cβ-hydroxylation of free l-Arg catalyzed by a member of the nonheme Fe2+- and α-ketoglutarate (αKG)-dependent dioxygenase family and (eventually) a dehydration-mediated cyclization process catalyzed by a distinct enzyme(s). Contrary to our initial expectation, the sole nonheme Fe2+- and αKG-dependent dioxygenase candidate Mur15 encoded within the muraymycin gene cluster is instead demonstrated to catalyze specific Cβ hydroxylation of the Leu residue to generate (2S,3S)-β-OH-Leu that is found in most muraymycin congeners. Importantly, and in contrast to known l-Arg-Cβ-hydroxylases, the Mur15-catalyzed reaction occurs after the NRPS-mediated assembly of the peptide scaffold. This late-stage functionalization affords the opportunity to exploit Mur15 as a biocatalyst, proof of concept of which is provided.

Synthesis and physiochemical property evaluation of carbamate derivatives of scutellarin methyl ester

A series of carbamate prodrugs of scutellarin methyl ester (4a-4e) were prepared in the presence of bis(trichloromethyl) carbonate (BTC) with scutellarin methyl esters and l-amino acid tert-butyl ester hydrochloride as starting materials. In vitro stability and aqueous solubility of target compounds were evaluated. The results indicated that compounds 4d and 4e have higher solubility and in vitro stability than scutellarin respectively.

Synthesis of hydrazine and azapeptide derivatives by alkylation of carbazates and semicarbazones

Hydrazine and azapeptide analogs were synthesized effectively by alkylation of alkylidene carbazates and semicarbazones. In comparisons of benzylidene, benzhydrylidene, and fluorenylidene tert-butyl carbazates in alkylations using bases of different pKb character, superior conversion was obtained using the fluorenone derivative. Mild alkylation conditions were found employing Et4NOH as base and used to convert fluorenylidene tert-butyl carbazate into 13 different protected hydrazines. Moreover, racemization was avoided during alkylation of fluorenylidene semicarbazide in the synthesis of aza-propargylglycinylphenylalanine tert-butyl ester, the protecting groups from which could be selectively removed.

Isocyanates, Part 4.10 Convenient Phosgene-Free Method for the Synthesis and Derivatization of Enantiopure α-Isocyanato Carboxylic Acid Esters

A novel phosgene-free procedure for the synthesis of α-isocyanato carboxylic acid esters starting from α-amino acid esters has been achieved. The isocyanates are obtained enantiomerically pure (> 99% ee) by a DMAP-catalyzed isocyanation with di-tert-butyl