The Structure of Telomycin

Biosynthetic Studies of Telomycin Reveal New Lipopeptides with Enhanced Activity

“…Telomycin ( 1 ) is a peptide antibiotic produced by Streptomyces canus C159, which was described as an effective antibiotic against Gram-positive pathogens when initially isolated at the Bristol-Myers Company (New York, USA) in the 1950s. − It was demonstrated to inhibit Staphylococcus aureus (SA) with a minimal inhibitory concentration (MIC) of 8 μg/mL and even penicillin-resistant SA with a slightly higher MIC . In the 1960s, a first partial structure of telomycin containing a permutation of three amino acids was published. , Two nuclear magnetic resonance (NMR) based studies on telomycin in 1973 provided the correct structure of the complex molecule. , Telomycin ( 1 , Chart ) is a cyclic depsipeptide which is composed of 11 amino acids including five non-proteinogenic ones. It is composed of a nonapeptide lactone ring formed between the 4 Thr hydroxyl group and the C-terminal carboxyl group. − Only a few reports on this compound were published after the structure of telomycin was elucidated, − and to date, the mode of action (MoA) is still unclear.…”

“…In the 1960s, a first partial structure of telomycin containing a permutation of three amino acids was published. , Two nuclear magnetic resonance (NMR) based studies on telomycin in 1973 provided the correct structure of the complex molecule. , Telomycin ( 1 , Chart ) is a cyclic depsipeptide which is composed of 11 amino acids including five non-proteinogenic ones. It is composed of a nonapeptide lactone ring formed between the 4 Thr hydroxyl group and the C-terminal carboxyl group. − Only a few reports on this compound were published after the structure of telomycin was elucidated, − and to date, the mode of action (MoA) is still unclear. However, studies on a truncated analogue of telomycin lacking an aspartic acid and hydroxylation of cis -3-hydroxyl-proline called LL-AO341 β 1 revealed that specific inhibition of DNA, RNA, protein, lipid, or peptidoglycan synthesis by LL-AO341 β 1 could not be detected.…”

On the Strain Energy in Cyclopropene and the Heat of Formation of the C3H3+ Ion

“…The relative mobilities (taking 4-hydroxyproline as unity) were: electrophoresis: 4-Hypro (1), alio-4-Hypro (1.15), IVA (1.15), IVB (0.83), "fast moving" Hypro (1.15), "slow moving" Hypro (0.83); paper chromatography (9b,9c): 4-Hypro (1,1), a//o-4-Hypro (1.35, 1), IVA (1.80, I. 29), IVB (1.16, 1.08), "fast moving" Hypro (1.80, 1.29), "slow moving" Hypro (1.16, 1.08).…”

Methods for the Chemical Synthesis of Noncoded α‐Amino Acids found in Natural Product Peptides

“…Both trans and cis diastereomers of 3-hydroxyprolines (3-OH Pro), (2S,3S)-hydroxylproline and (2R,3S)-proline, respectively, are two of the most frequently occurring unusual nonproteinogenic CAAs isolated from peptide natural products and complex alkaloids such as castanospermine [21], slaframine [22], detoxinine [23,24], mucrorin D [25], telomycin [26], and polyhydroxylated alkaloids [27]. In particular, castanospermines, slaframine, and detoxinine are known as potent glycosidase inhibitors [28,29], where their analogs serve as lead compounds in the development of novel antiviral agents.…”