The stereospecific synthesis of ‘orthogonally’ protected lanthionines

Swali, Vinay; Matteucci, Mizio; Elliot, Richard; Bradley, Mark

doi:10.1016/s0040-4020(02)01091-8

Cited by 20 publications

(18 citation statements)

References 38 publications

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“…The same year, the method of Dugave and Ménez (Scheme ) was also adapted by Swali and co‐workers for the SPPS with orthogonally protected Lan (Scheme ) …”

Section: Chemical Synthesis Of Protected Lanthioninescontrasting

confidence: 76%

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Progress in Lanthionine and Protected Lanthionine Synthesis

Denoël

Lemaire

Luxen

2018

Chemistry A European J

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Lanthionine (Lan), a non‐proteinogenic natural amino acid, is an essential component of peptidoglycan found in the cell wall of Fusobacterium species. Lan and β‐methyllanthionine are also key constituents in lantibiotics, a prevalent class of peptide antibiotics. The development of those new antibacterial drugs with enhanced properties is the focus of recent research. Since multiple isomers of Lan are possible, a regio‐ and diastereoselective synthesis is challenging. This comprehensive review summarizes the known chemical syntheses of lanthionine from various precursors (e.g., β‐chloroalanine, cystine, dehydroalanine, β‐iodoalanine, aziridine, serine lactone, sulfamidate) since 1941. Methods for preparation of unprotected, protected, orthogonally protected, and mutually orthogonally protected lanthionine with relevant experimental details and perspectives on their usefulness are provided. The potential of these Lan derivatives is illustrated by one recent application.

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“…The same year, the method of Dugave and Ménez (Scheme ) was also adapted by Swali and co‐workers for the SPPS with orthogonally protected Lan (Scheme ) …”

Section: Chemical Synthesis Of Protected Lanthioninescontrasting

confidence: 76%

“…In 2002 and 2003 Swali et al and Mohd Mustapa et al independently investigated the synthesis of protectedL an 104 throughaMitsunobu reaction. [56] For this reaction, the low reactivity of the thiol was increased by using am ixture of PMe 3 and 1,1'-(azodicarbonyl)dipiperidine (ADDP) (Scheme 25).…”

Section: Synthesis From Serinementioning

confidence: 99%

Progress in Lanthionine and Protected Lanthionine Synthesis

Denoël

Lemaire

Luxen

2018

Chemistry A European J

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“…The S-alkylation procedure may appear as a slight modification of a method already reported for the synthesis of lanthionine derivatives. [17][18][19] Indeed, the resemblance is only formal, since in our case the S-alkylation occurs on an iodide β to a carbamate function (N-Boc-β-iodoamines 5) whereas the cysteine alkylation leading to lanthionines occurs on the β-iodide of N-trityl-protected serine alkyl ester that is naturally prone to undergo either hydrogen iodide elimination or aziridine ring closure.…”

Section: Resultsmentioning

confidence: 91%

One‐Pot Synthesis of Orthogonally Protected Enantiopure S‐(Aminoalkyl)cysteine Derivatives

et al. 2005

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The general synthesis of a new class of non-natural diamino acids, 2-amino-3-[(2Ј-aminoalkyl)thio]propanoic acids or S-(aminoalkyl)cysteines, is reported. Under the conditions devised, enantiopure N-Boc-protected β-iodoamines, readily generated from proteinogenic α-amino acids, are treated with L-cysteine ethyl ester hydrochloride, using Cs 2 CO 3 as a base. The S-alkylation products, obtained in high yields (96-98 %) and without any detectable traces of accompanying

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“…Our particular interest in labionin synthesis is driven by the need for new labionin analogues which cannot be accessed by biosynthetic manipulations. Previously, there have been published a number of elegant strategies for the synthesis and assembly of lanthionines5–7 and lantibiotics8–11, respectively. However, none of those approaches seem to be applicable to the synthesis of labionin.…”

Section: Introductionmentioning

confidence: 99%

Synthetic studies toward labionin, a new α,α‐disubstituted amino acid from type III lantibiotic labyrinthopeptin A2

Sambeth

Süssmuth

2011

Journal of Peptide Science

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The labyrinthopeptins are a new class of lantibiotics containing two identical quaternary α,α-disubstituted amino acids, named labionin (Lab). The synthetic formation of this unique structural feature represents the key step in the total synthesis of these polycyclic peptides. In this report we describe the synthesis of an orthogonally protected α,α-disubstituted amino acid building block serving as labionin precursor for the future assembly of labyrinthopeptin A2 and of other labyrinthopeptin derivatives.

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The stereospecific synthesis of ‘orthogonally’ protected lanthionines

Cited by 20 publications

References 38 publications

Progress in Lanthionine and Protected Lanthionine Synthesis

Progress in Lanthionine and Protected Lanthionine Synthesis

One‐Pot Synthesis of Orthogonally Protected Enantiopure S‐(Aminoalkyl)cysteine Derivatives

Synthetic studies toward labionin, a new α,α‐disubstituted amino acid from type III lantibiotic labyrinthopeptin A2

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