503565-01-3

Upstream product

• 508189-54-6 (2R)-serine allyl ester 
• 503565-00-2 N-triphenylmethyl-(R)-serine(O-methanesulfonyl) allyl ester 
• 76-83-5 trityl chloride 
• 503564-99-6 (R)-allyl 3-hydroxy-2-(tritylamino)propanoate 
• 150094-69-2 N-triphenylmethyl-(R)-serine 

Downstream Products

• 503565-02-4 (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester 
• 618097-75-9 (R)-1-triphenylmethylaziridine-2-carboxylic acid allyl ester 

Relevant academic research and scientific papers

Orthogonally protected lanthionines: Synthesis and use for the solid-phase synthesis of an analogue of nisin ring C

(Chemical Equation Presented) Lanthionine, a thioether analogue of cystine, is a key component of the lantibiotics, a family of modified peptides bearing multiple thioether bridges resulting from posttranslational modifications between side chains. It is also used as a conformational constraint in medicinally active peptides. We have explored two synthetic routes to give lanthionine, orthogonally protected with Alloc/allyl and Fmoc groups. One route utilized a carbamate-protected iodoalanine that yielded a mixture of diastereoisomers, and one utilized a trityl-protected iodoalanine, formed via a Mitsunobu reaction, that gave the single desired lanthionine, in complete regio-and diastereoselectivity. We then used this orthogonally protected lanthionine in the solid-phase synthesis of an analogue of a fragment of nisin containing its ring C. The chemoselective deprotection of the allyl and Alloc groups of the incorporated lanthionine unit was followed by regio- and stereoselective cyclization on resin to give the desired lanthionine-bridged peptide.

Synthesis of orthogonally protected lanthionines

Synthetic approaches to the lantibiotics, a family of thioether-bridged antimicrobial peptides, require flexible synthetic routes to a variety of orthogonally protected derivatives of lanthionine 1. The most direct approaches to lanthionine involve the re

The stereospecific synthesis of 'orthogonally' protected lanthionines

Lanthionine is an attractive monomer for the design and synthesis of novel conformationally constrained peptidomimetics, since unlike cystine, the monosulfur bridge of lanthionine is chemically far more robust and also displays a greater degree of conformational rigidity. The synthesis of lanthionine residues for use in peptide synthesis is non-trivial due to the protectional requirements necessary for this tetra-functional amino acid. In this paper an efficient stereo-specific route to orthogonally protected lanthionine is described.

Synthesis of orthogonally protected lanthionines: A reassessment of the use of alanyl β-cation equivalents

Whilst developing a strategy for the solid-phase synthesis of lanthionine-containing peptides, we became aware of some problems with a previously published route for the synthesis of orthogonally-protected lanthionine. We report a structural reassignment