15917-28-9

Basic information

• Product Name: (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester
• CAS NO: 15917-28-9
• Molecular Weight: 209.245
• Mol File: 15917-28-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester(15917-28-9)
• EPA Substance Registry System: (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester(15917-28-9)

Safety Data

• Hazardous Substances Data: 15917-28-9(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 7352-06-9 (2R;3R)-2-amino-3-hydroxy-3-phenylpropionic acid 
• 60317-41-1 ethyl 2-(hydroxyimino)-3-oxo-3-phenylpropanoate 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 6966-29-6 N-acetyl-erythro-DL-β-phenylserine ethyl ester 
• 78605-23-9 ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate 
• 123-72-8 butyraldehyde 
• 69-96-5 dl-threo-phenylserine 
• 464913-97-1 5-(α-hydroxy-benzyl)-2,2-dimethyl-imidazolidin-4-one 
• 106270-15-9 (+/-)-2-methyl-5t-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid ethyl ester 
• 860259-89-8 5,5-dimethyl-1,3-diphenyl-tetrahydro-imidazo[1,5-c]oxazol-7-one 
• 100-52-7 benzaldehyde 

Downstream Products

• 3306-06-7 (1RS,2SR)-2-amino-1-phenyl-propane-1,3-diol 
• 17193-35-0 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid amide 
• 101599-24-0 (2RS,3RS)-2-cyclohexylidenamino-3-hydroxy-3-phenyl-propionic acid ethyl ester 
• 577-41-3 (2RS,3RS)-3-hydroxy-3-phenyl-2-(2,2,2-trifluoro-acetylamino)-propionic acid ethyl ester 
• 100714-04-3 (2RS,3SR)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-phenyl-propionic acid ethyl ester 
• 13789-59-8 (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionohydroxamic acid 
• 100861-23-2 (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid hydrazide 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 24218-51-7 (1RS,2RS)-2-benzylidenamino-1-phenyl-propane-1,3-diol 
• 100610-67-1 (2RS,3SR)-3-hydroxy-2-methylsulfanylcarbonylamino-3-phenyl-propionic acid ethyl ester 
• 101730-06-7 (RS)-((2Ξ,4RS)-3-acetyl-2-phenyl-oxazolidin-4-yl)-phenyl-methanol 
• 100381-15-5 3-chloro-2-(2,2-dichloro-acetylamino)-3-phenyl-propionic acid ethyl ester 
• 53732-41-5 (+/-)-(2-methyl-5t-phenyl-4,5-dihydro-oxazol-4r-yl)-methanol 
• 46506-67-6 (2RS,3SR)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid 

Relevant articles and documents

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.

Enantioselektive Synthese von D-threo-β-Hydroxy-α-aminosaeuren mit Titan-Kohlenhydrat-Komplexen

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