112139-12-5

Basic information

• Product Name: (S)-((S)-2-Benzyloxycarbonylamino-octanoylamino)-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid
• CAS NO: 112139-12-5
• Molecular Weight: 562.577
• Mol File: 112139-12-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-((S)-2-Benzyloxycarbonylamino-octanoylamino)-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-((S)-2-Benzyloxycarbonylamino-octanoylamino)-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid(112139-12-5)
• EPA Substance Registry System: (S)-((S)-2-Benzyloxycarbonylamino-octanoylamino)-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid(112139-12-5)

Safety Data

• Hazardous Substances Data: 112139-12-5(Hazardous Substances Data)

Upstream product

• 76313-08-1 (+/-)-N-(benzyloxycarbonyl)-α-aminooctanoic acid 
• 2623-82-7 2-bromooctanoic acid 
• 644-90-6 2-aminooctanoic acid 
• 24695-48-5 1-(5'-amino-5'-deoxy-α-D-allofuranuronosyl)uracil 
• 112139-11-4 (+/-)-p-nitrophenyl N-(benzyloxycarbonyl)-α-aminooctanoate 

Relevant articles and documents

Synthesis and anticandidal properties of polyoxin L analogues containing α-amino fatty acids

Analogues of polyoxin L containing amino acids with saturated fatty acid like side chains were synthesized from the benzyloxycarbonyl-protected α-amino fatty acid p-nitrophenyl ester and uracil polyoxin C. Transfer hydrogenolysis using palladium black and formic acid gave diastereomeric, dipeptidyl polyoxin L analogues containing α-aminooctanoic acid (3), α-aminododecanoic acid (4), or α-aminohexadecanoic acid (5) as the amine terminal residue in 40-60% yield. Diastereomers of 3 and 5 were resolved by using high-performance liquid chromatography on a reversed-phase column and designated as 3a, 3b and 5a, 5b. Analogues 3-5 were excellent inhibitors of chitin synthetase from Candida albicans; 4, the best inhibitor, had an ID50 of 0.5 μM. The L,L diastereomers of 3 and 5 were 1-2 orders of magnitude more potent chitin synthetase inhibitors than their D,L homologues. None of the synthetic polyoxin L analogues inhibited transport of trimethionine, but 3a, 4, and 5b caused decreases of 71%, 87%, and 83%, respectively, in the initial rate of uptake of dileucine. Compounds 3-5 were significantly more stable to peptidase degradation than polyoxin L analogues containing naturally occurring α-amino acids. Compound 4 inhibited growth of C. albicans in culture at 40-80 μg/mL. All other analogues were less potent antifungals. The results suggest that synthetic polyoxins can be designed to have increased affinity for a peptide transport system and to have increased stability against intracellular degradation in C. albicans.