934349-41-4

Upstream product

• 883143-12-2 (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 934349-42-5 (2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 
• 934349-53-8 C₅₁H₅₉N₅O₁₂ 
• 1015422-17-9 C₄₁H₅₇N₅O₁₂ 
• 1015422-29-3 C₄₁H₅₆N₄O₁₃ 
• 934349-43-6 trifluoromethanesulfonyloxy-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 934349-44-7 benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 934349-45-8 (2R)-methyl 2-azido-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate 

Relevant academic research and scientific papers

Synthesis of glucose-templated lysine analogs and incorporation into the antimicrobial dipeptide sequence kW-OBn

The synthesis of two glucose-templated (GlcT) lysine analogs GlcTK and GlcTk in which the side chain of d- and l-lysine (k and K) is conformationally constrained via incorporation into a d-glucose scaffold is described. A key-step in the synthesis is a high yielding, reductive ring opening of an exocyclic glucose-derived epoxide to form a α-hydroxy ester that can be converted into GlcTK and GlcTk. To demonstrate the use of these building blocks in peptide synthesis, we replaced d-lysine in the antimicrobial dipeptide sequence kW-OBn (W = l-tryptophan) and determined the antibacterial activity against various gram-positive and gram-negative organisms. Our results show that the replacement of d-lysine by unprotected GlcTk in dipeptide kW-OBn results in reduced antibacterial activity.

Synthesis of Carbohydrate-Templated Amino Acids and Methods of Using Same

The present invention generally relates to tetrahydropyranyl-derivatized amino acids, their syntheses and their incorporation into peptides and peptidomimetics. The tetrahydropyran moiety constrains the side chain of an amino acid, thereby providing a molecule that may act as a sugar- or amino acid-mimetic as well as a scaffold for combinatorial synthesis.

Synthesis of sugar-lysine chimera with integrated gluco-configured 1,3-hydroxyamine motif

The paper describes the synthesis of glucose-configured sugar-lysine chimeras in which the side chain of lysine is conformationally constrained via incorporation into a D-glucose scaffold. Key step in the synthesis is a high-yielding, reductive ring opening of an exocyclic glucose-derived epoxide to form an α-hydroxyester that can be converted into chimeric sugar-lysine analogues. To demonstrate the use of these novel chimeric sugar-lysine building blocks in peptide coupling, we replaced D-lysine in the antimicrobial dipeptide sequence kW by a D-glucose-D-lysine chimera. Georg Thieme Verlag Stuttgart.