15005-62-6

Basic information

• Product Name: bottromycin A(2)
• Synonyms: bottromycin A(2);b-Alanine, N-[(2S)-2-[[glycyl-(3R)-3-methyl-Lprolyl-L-valyl]amino]-1-imino-3,3-dimethylbutyl]-3-methyl-L-valyl-(bS)-b-methyl-L-phenylalanyl-3-(2-thiazolyl)-, methyl ester, cyclic (1')-imine,(3R)-
• CAS NO: 15005-62-6
• Molecular Formula: C₄₂H₆₂N₈O₇S
• Molecular Weight: 823.06
• Mol File: 15005-62-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 1061.3°Cat760mmHg
• Flash Point: 595.7°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: bottromycin A(2)(CAS DataBase Reference)
• NIST Chemistry Reference: bottromycin A(2)(15005-62-6)
• EPA Substance Registry System: bottromycin A(2)(15005-62-6)

Safety Data

• Hazardous Substances Data: 15005-62-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C42H62N8O7S/c1-23(2)30-36(53)49-33(41(5,6)7)35(44-22-28(51)50-19-17-24(3)32(50)38(55)46-30)48-34(42(8,9)10)39(56)47-31(25(4)26-15-13-12-14-16-26)37(54)45-27(21-29(52)57-11)40-43-18-20-58-40/h12-16,18,20,23-25,27,30-34H,17,19,21-22H2,1-11H3,(H,44,48)(H,45,54)(H,46,55)(H,47,56)(H,49,53)

Upstream product

• 1138161-40-6 (R)-3-[(2S,3S)-2-azido-3-phenylbutyrylamino]-3-(thiazol-2-yl)propionic acid methyl ester 
• 128677-95-2 (2S,3S)-2-azido-3-phenylbutanoic acid 
• 1138161-38-2 (S(S),R)-allyl methyl [N-(p-toluenesulfinyl)amino(thiazol-2-yl)methyl]malonate 
• 76362-53-3 (R)-methyl 3-amino-3-(thiazol-2-yl)propanoate 
• 1138161-39-3 (S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate 
• 1138161-46-2 N-{N-tert-butoxycarbonyl-[(3R)-3-methyl-L-prolinyl]-L-valinyl-[L-(carboxymethylimino)-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-62-2 N-{N-tert-butoxycarbonyl-[(3R)-3-methyl-L-prolinyl]-L-valinyl-[L-(2-hydroxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-45-1 N-{N-tert-butoxycarbonyl-[(3S)-3-methyl-L-prolinyl]-L-valinyl-[L-(2-tert-butyldiphenylsilyloxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-44-0 N-{N-tert-butoxycarbonyl-L-valinyl-[L-(2-tert-butyldiphenylsilyloxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-60-0 C₄₇H₆₆N₆O₅SSi 
• 1138161-43-9 N-{[N-phthaloyl-L-(2-tert-butyldiphenylsilyloxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-41-7 N-{L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-59-7 N-{N'-tert-butoxycarbonyl-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 

Downstream Products

• 66854-34-0 (R)-3-[(2S,3S)-2-amino-3-phenylbutyrylamino]-3-(thiazol-2-yl)propanoic acid methyl ester 
• 1138161-35-9 C₂₅H₄₁N₅O₄ 
• 937729-48-1 N-{[(3R)-3-methyl-L-prolinyl]-L-valinyl-[L-(2-hydroxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester 

Relevant articles and documents

Synthesis and Evaluation of Antibacterial Activity of Bottromycins

Total synthesis of bottromycin A2 can be accomplished through a diastereoselective Mannich reaction of a chiral sulfinamide, mercury-mediated intermolecular amidination, and cyclization of a constrained tetracyclic peptide. Exploitation of this process allowed the synthesis of several novel bottromycin analogs. The antimicrobial activity of these analogs was evaluated in vitro against Gram-positive bacteria, such as methicillin resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococci (VRE). Structure-activity relationships were explored taking into consideration the unique three-dimensional structure of the compounds. Notably, one of the new analogs devoid of a methyl ester, which is known to lower the in vivo efficacy of bottromycin, exhibited antibacterial bioactivity comparable to that of vancomycin.