19396-05-5

Upstream product

• 52471-68-8 (2S,3S,4S)-2-Azido-3,4-bis-benzyloxy-5-carbamoyloxy-pentanoic acid 
• 90661-54-4 5-O-(aminocarbonyl)-2-[((1,1-dimethylethyl)oxycarbonyl)amino]-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid 
• 37362-29-1 polyoxin N 
• 90661-54-4 (3S,4S)-5-<(aminocarbonyl)oxy>-N-<(1,1-dimethylethoxy)carbonyl>-3,4-<(1-methylethylidene)dioxy>-D-norvaline 
• 22886-47-1 (2S,4R)-2-Amino-5-carbamoyloxy-4-hydroxy-pentanoic acid 
• 52471-73-5 (2S,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxycarbonylamino-5-carbamoyloxy-pentanoic acid 
• 105281-26-3 N-[(S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl]-4-chloro-benzamide 
• 152390-97-1 N-Benzyl-N-[(S)-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-furan-2-yl-methyl]-hydroxylamine 
• 152390-99-3 [(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-furan-2-yl-methyl]-carbamic acid tert-butyl ester 
• 152391-01-0 [(S)-((4S,5S)-5-Carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-furan-2-yl-methyl]-carbamic acid tert-butyl ester 
• 152391-00-9 (1S)-1-(tert-butoxycarbonylamino)-1-deoxy-1-(2-furyl)-2,3-O-isopropylidene-L-threitol 

Relevant academic research and scientific papers

Deciphering Carbamoylpolyoxamic Acid Biosynthesis Reveals Unusual Acetylation Cycle Associated with Tandem Reduction and Sequential Hydroxylation

Polyoxin, produced by Streptomcyes cacaoi var. asoensis and Streptomyces aureochromogenes, contains two non-proteinogenic amino acids, carbamoylpolyoxamic acid (CPOAA) and polyoximic acid. Although the CPOAA moiety is highly unusual, its biosynthetic logic has remained enigmatic for decades. Here, we address CPOAA biosynthesis by reconstitution of its pathway. We demonstrated that its biosynthesis is initiated by a versatile N-acetyltransferase, PolN, catalyzing L-glutamate (1) to N-acetyl glutamate (2). Remarkably, we verified that PolM, a previously annotated dehydrogenase, catalyzes an unprecedented tandem reduction of acyl-phosphate to aldehyde, and subsequently to alcohol. We also unveiled a distinctive acetylation cycle catalyzed by PolN to synthesize α-amino-δ-hydroxyvaleric acid (6). Finally, we report that PolL is capable of converting a rare sequential hydroxylation of α-amino-δ-carbamoylhydroxyvaleric acid (7) to CPOAA. PolL represents an intriguing family of Fe(II)-dependent α-ketoglutarate dioxygenase with a cupin fold. These data illustrate several novel enzymatic reactions, and also set a foundation for rational pathway engineering for polyoxin production.

A concise synthesis of (+)-polyoxamic acid and (+)-5-O-carbamoyl polyoxamic acid

We report the concise synthesis of (+)-polyoxamic acid and (+)-5-O-carbamoyl polyoxamic acid from L-xylose in seven or six steps, respectively. The key steps include a diastereoselective amination of syn-1,2-polybenzyl ethers using chlorosulfonyl isocyanate (CSI) and the one-pot introduction of carbamates into the allylic benzyl ether and primary hydroxyl moieties. Georg Thieme Verlag Stuttgart.

Stereocontrol by diethylaluminum chloride in the addition of 2-lithiofuran and N-methyl-2-lithioimidazole to αalkoxy nitrones. Total synthesis of 5-O-carbamoylpolyoxamic acid

The addition of the title metalated heterocycles 1 to the nitrone 2 derived from D-glyceraldehyde acetonide leads to the corresponding syn-adducts as major products (ds 88-96 %) while the reaction in the presence of Et2AlCl leads to anti isomer