503565-02-4

Basic information

• Product Name: (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester
• Synonyms: (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester
• CAS NO: 503565-02-4
• Molecular Weight: 768.974
• Mol File: 503565-02-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester(503565-02-4)
• EPA Substance Registry System: (2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester(503565-02-4)

Safety Data

• Hazardous Substances Data: 503565-02-4(Hazardous Substances Data)

Upstream product

• 508189-54-6 (2R)-serine allyl ester 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 540-88-5 acetic acid tert-butyl ester 
• 503564-99-6 (R)-allyl 3-hydroxy-2-(tritylamino)propanoate 
• 150094-69-2 N-triphenylmethyl-(R)-serine 
• 76-83-5 trityl chloride 
• 172322-96-2 (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-mercaptopropanoate 
• 503565-01-3 N-triphenylmethyl-β-iodo-(S)-alanine allyl ester 
• 503565-00-2 N-triphenylmethyl-(R)-serine(O-methanesulfonyl) allyl ester 
• 139592-37-3 (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) 
• 62574-13-4 L-cystine tert-butyl ester 

Relevant articles and documents

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.

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.