74144-16-4

Basic information

• Product Name: Hexaaxetylcelenamid A
• Synonyms: Hexaaxetylcelenamid A
• CAS NO: 74144-16-4
• Molecular Weight: 974.816
• Mol File: 74144-16-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Hexaaxetylcelenamid A(CAS DataBase Reference)
• NIST Chemistry Reference: Hexaaxetylcelenamid A(74144-16-4)
• EPA Substance Registry System: Hexaaxetylcelenamid A(74144-16-4)

Safety Data

• Hazardous Substances Data: 74144-16-4(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 74144-98-2 Celenamide A 
• 93862-80-7 <(S)-N-Acetylleucyl>-<(Z)-3,4,5-triacetoxy-α,β-didehydrophenylalanyl>-<(S)-6-brom-N-<2-(3,4-diacetoxyphenyl)-2-(4-nitrophenylseleno)ethyl>tryptophanamid> 
• 71932-18-8 3,4,5-tri-O-acetylbenzaldehyde 
• 93862-77-2 3-{(S)-2-[2-((S)-2-Acetylamino-4-methyl-pentanoylamino)-2-(dimethoxy-phosphoryl)-acetylamino]-2-tert-butoxycarbonyl-ethyl}-6-bromo-indole-1-carboxylic acid tert-butyl ester 
• 860572-47-0 1-(3,4-diacetoxy-phenyl)-2-diazo-ethanone 
• 58534-64-8 3,4-Diacetoxy-benzoesaeure 
• 100945-19-5 2-chloro-1-[3,4-bis(acetyloxy)phenyl]ethanone 
• 1188-21-2 N-Ac-Leu 
• 6635-24-1 3,4,5-triacetoxybenzoic acid 
• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 57929-25-6 3,4-(diacetyloxy)benzoyl chloride 
• 52415-29-9 6-bromo-1H-indole 

Downstream Products

• 74144-20-0 2-Acetylamino-4-methyl-pentanoic acid [(Z)-1-[2-(6-bromo-1H-indol-3-yl)-1-carbamoyl-ethylcarbamoyl]-2-(3,4,5-trimethoxy-phenyl)-vinyl]-amide 
• 74144-24-4 2-Acetylamino-4-methyl-pentanoic acid [(Z)-1-[2-(6-bromo-1H-indol-3-yl)-1-carbamoyl-ethylcarbamoyl]-2-(3,4,5-trihydroxy-phenyl)-vinyl]-amide 
• 74144-22-2 Acetic acid 2,3-diacetoxy-5-{(Z)-2-(2-acetylamino-4-methyl-pentanoylamino)-2-[2-(6-bromo-1H-indol-3-yl)-1-carbamoyl-ethylcarbamoyl]-vinyl}-phenyl ester 

Relevant articles and documents

Syntheses of Peptide Alkaloids, 11. - Amino Acids and Peptides, 51. - Dehydroamino Acids, 19. - Total Synthesis of Hexaacetylcelenamide A

The total synthesis of the linear peptide alkaloid hexaacetylcelenamide A (7) is described.Key steps are two condensation reactions with α-dialkylphosphoryl amino acid derivatives 10 to obtain the dehydroamino acid and dehydro peptide derivatives 14 and 17, respectively.

Celenamides A and B, Linear Peptide Alkaloids from the Sponge Cliona celata

Two novel linear peptide alkaloids have been isolated as their hexaacetyl derivatives from acetylated methanol extracts of the sponge Cliona celata.The structures of hexaacetylcelenamide A (3) and B (4) were established by spectroscopic analysis and chemical degradation by ozonolysis and acid-catalyzed hydrolysis.The unique amino acid α,β-didehydro-3,4,5-trihydroxyphenylalanine was shown to be a subunit of both 3 and 4.A small-scale isolation employing acetic-d6 anhydride as the acetylating agent indicated that celenamides A (1) and B (2) were the naturally occurring sponge metabolites.