911475-69-9

Upstream product

• 64-17-5 ethanol 
• 6254-48-4 (2S,3R)-3-phenylserine 
• 100-52-7 benzaldehyde 
• 1072879-63-0 N-phenylmethylidene-1,1-bis(4-methoxy-3,5-dimethylphenyl)methylamine 
• 4192-77-2 ethyl cinnamate 
• 130517-77-0 Butyric acid (1S,2S)-2-bromo-2-ethoxycarbonyl-1-phenyl-ethyl ester 
• 62355-67-3 ethyl (+/-)-(2R,3R)-2-bromo-3-hydroxy-3-phenylpropanoate 
• 78605-23-9 ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate 
• 123-72-8 butyraldehyde 
• 130517-91-8 (2S,3R)-2-Azido-3-hydroxy-3-phenyl-propionic acid ethyl ester 

Downstream Products

• 119594-47-7 ethyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate 
• 1345116-62-2 (6R,8S,11S,14S)-ethyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate 
• 1345116-59-7 C₂HF₃O₂*C₁₅H₂₂N₂O₄ 
• 1345116-55-3 (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate 
• 1345116-67-7 (6R,8S,11R,14S)-methyl 8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oate 
• 1345116-64-4 (6R,8S,11S,14S)-8-(tert-butoxycarbonyl(methyl)amino)-14-((R)-methoxy(phenyl)methyl)-2,2,6,11-tetramethyl-9,12-dioxo-3,3-diphenyl-4-oxa-10,13-diaza-3-silapentadecan-15-oic acid 
• 855315-44-5 (6S,9R,12S)-methyl 6-((R)-3-(benzoyloxy)-2-methylpropyl)-12-((R)-methoxy(phenyl)methyl)-2,2,5,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate 
• 1346156-35-1 (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate 
• 6966-29-6 (2S,3R)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Stereochemistry and conformation of skyllamycin, a non-ribosomally synthesized peptide from streptomyces sp. Acta 2897

Skyllamycin is a non-ribosomally synthesized cyclic depsipeptide from Streptomyces sp. Acta 2897 that inhibits PDGF-signaling. The peptide scaffold contains an N-terminal cinnamoyl moiety, a β-methylation of aspartic acid, three β-hydroxylated amino acids and one rarely occurring α-hydroxy glycine. With the exception of α-hydroxy glycine, the stereochemistry of the amino acids was assigned by comparison to synthetic reference amino acids applying chiral GC-MS and Marfey-HPLC analysis. The stereochemistry of α-hydroxy glycine, which is unstable under basic and acidic conditions, was determined by conformational analysis, employing a combination of data from NOESY-NMR spectroscopy, simulated annealing and free MD simulations. The simulation procedures were applied for both R- and S-configured α-hydroxy glycine of the skyllamycin structure and compared to the NOESY data. Both methods, simulated annealing and free MD simulations independently support S-configured α-hydroxy glycine thus enabling the assignment of all stereocenters in the structure of skyllamycin and devising the role of two-component flavin dependent monooxygenase (Sky39) as S-selective.

CHEMO-ENZYMATIC SYNTHESIS OF ALL ISOMERIC 3-PHENYLSERINES AND -ISOSERINES

The synthesis of all isomers of 3-phenylserines and 3-phenylisoserines in enantiomerically pure form is presented.Diastereomerically pure educts (threo/erythro-2-azido-3-butanoyloxy-3-phenyl-propionic esters, threo/erythro-3-azido-2-butanoyloxy-3-phenylpropionic esters, threo-2-butanoylamino-3-butanoyloxy-3-phenylpropionic ester, erythro-3-butanoylamino-2-butanoyloxy-3-phenyl-propionamide) were prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps.These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines.The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic esters was investigated.