Total synthesis and NMR conformational study of signal peptidase II inhibitors, globomycin and SF-1902 A5

Kiho, Toshihiro; Nakayama, Mizuka; Kogen, Hiroshi

doi:10.1016/s0040-4020(03)00110-8

Cited by 19 publications

(13 citation statements)

References 34 publications

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“…[223][224][225][226][227] The latter problem is usually solved (Scheme 27) by performing the macrolactonization on the ynoic seco-acid and then reducing the triple bond, as illustrated in the synthesis of laulimalide. 227 To date, the Yamaguchi protocol and variations have been used in more than 200 synthetic applications, including eightmembered lactones; 228,229 nine-membered halicholactone 230,231 and a nine-membered intermediate to laurencin; 232 10-membered didemninlactone, 233 decarestricine, 234 mueggelone, 235,236 hebarumin, 237 and ascidiatrienolide; 238 cyclodepsipeptides such as geodiamolide, 342 globomycin, 343 and stevastelin; 344 nonactin [345][346][347][348] aspicilin; 293,349-352 44-membered swhinholide; 72,[353][354][355] acutiphycin; 356,357 scytophycin; 69,358,359 aplyronine A; 67,360-362 aplyolide; 363,364 hygrolidin; 198 nargenicin and dinemycin A precursors; 365,366 bafilomycin, where the Mukaiyama, Keck, and Palomo protocols failed; 367 apoptolidinone; 61,62,368,369 conglobatin; 209 and macrocyclic glycolipids, 12 such as tric...…”

Section: Mixed Anhydrides and Basic Activationmentioning

confidence: 99%

Macrolactonizations in the Total Synthesis of Natural Products

2006

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Section: Mixed Anhydrides and Basic Activationmentioning

confidence: 99%

Macrolactonizations in the Total Synthesis of Natural Products

2006

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“…Due to the structure of fatty acid chains and the sequence of amino acids were the significant influencing factors of the biological activities, the structural analysis of lipopeptides had been paid much attention [25]. The structural characterization of a lipopeptide was commonly distributed into two parts, including analysis of the fatty acid chain and the composition and sequence of the peptide chain.…”

Section: Introductionmentioning

confidence: 99%

Structural characterization of lipopeptides from Enterobacter sp. strain N18 reveals production of surfactin homologues

You

Yang

2015

Euro J Lipid Sci & Tech

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Lipopeptides are amphiphilic biosurfactants which contain fatty acid chains and peptide chains. A novel lipopeptide producer was isolated from soil samples and identified as Enterobacter sp. by using 16S rRNA gene sequencing. The surface tension of the cell-free broth decreased from 58.0 mN/m to 27.9 mN/m after the strain was incubated for 48 h at 37°C. The fatty acid part of the lipopeptide was elucidated by ESI-MS and GC-MS after methyl esterification, which showed that fatty acids were mixtures of n-C 12 , iso-C 13 , anteiso-C 13 , iso-C 14 , n-C 14 , iso-C 15 , anteiso-C 15 , iso-C 16, n-C 16 and iso-C 17 b-hydroxy fatty acids. The peptide sequence, of which the composition of amino acids was determined by GC-MS with trimethylsilylation, was deduced to be N-Glu-Leu-Leu-Val-Asp-Leu-Leu-C by using Q-TOF MS/MS. The fatty acid chain was bonded to the N-terminal of the peptide moiety, and a cyclic ring was constituted by the hydroxyl group of the fatty acid chain and the C-terminal.Practical applications: The systematic characterization methods used in this article are helpful for structural analysis of those lipopeptide-like compounds. The information of Enterobacter-produced surfactin helps us to enlarge the family of surfactin-producers and expand the recognition of metabolites of Enterobacter spp.

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“…Second, one amino acid is replaced by the other amino acid such as the smaller Val being replaced by Leu or Ile [13] [18] [27]. Third, an additional Me group may be linked to one of the N-atoms or CH 2 group of peptides [28] [29]. Fourth, one of the carboxy groups of amino acid residues such as Glu or Asp is methylated [18].…”

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confidence: 99%

Structural Characterization of Lipopeptide Methyl Esters Produced by Bacillus licheniformis HSN 221

Yang

2010

Chemistry & Biodiversity

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Lipopeptides and their analogues are of increasing interest due to their amphiphilic structures and potential applications in various fields. Three purified lipopeptides analogues were obtained at the same time after two-step column-chromatographic purification from cell-free broth cultivated by Bacillus licheniformis HSN 221. Analysis by ESI-MS, GC/MS, HPLC, and Q-TOF MS/MS revealed their primary structures as anteiso-C(15)- and iso-C(15)-beta-hydroxy fatty acid-Gln-Leu-Leu-Val-MeAsp-Leu-Ile, anteiso-C(15)- and iso-C(15)-beta-hydroxy fatty acid-MeGlu-Leu-Leu-Val-Asp-Leu-Ile and iso-C(16)-beta-hydroxy fatty acid-Glu-Leu-Leu-Val-MeAsp-Leu-Ile, respectively. The production of two surfactin monomethyl esters and one lichenysin monomethyl ester directly from microorganisms is helpful to understand the variants of metabolites.

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Total synthesis and NMR conformational study of signal peptidase II inhibitors, globomycin and SF-1902 A5

Cited by 19 publications

References 34 publications

Macrolactonizations in the Total Synthesis of Natural Products

Macrolactonizations in the Total Synthesis of Natural Products

Structural characterization of lipopeptides from Enterobacter sp. strain N18 reveals production of surfactin homologues

Structural Characterization of Lipopeptide Methyl Esters Produced by Bacillus licheniformis HSN 221

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