851857-30-2

Basic information

• Product Name: (2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid
• CAS NO: 851857-30-2
• Molecular Weight: 626.615
• Mol File: 851857-30-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid(851857-30-2)
• EPA Substance Registry System: (2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid(851857-30-2)

Safety Data

• Hazardous Substances Data: 851857-30-2(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 25878-60-8 D-galactose pentaacetate 
• 504-91-6 (5R)-5-hydroxy-L-lysine 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 

Downstream Products

• 270089-67-3 (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine 

Relevant articles and documents

Probing molecular interactions within class II MHC Aq/ glycopeptide/T-cell receptor complexes associated with collagen-induced arthritis

T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex Aq molecule. We report a comparative model of Aq in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala261 and Gly262 in the glycopeptide was selected for replacement with ψ[COCH2], ψ[CH2NH 2+], and ψ[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the Aq molecule, and the results were interpreted in view of the AVglycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A q/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.

9-BBN as a convenient protecting group in functionalisation of hydroxylysine

9-BBN was used for regioselective protection of the α-amino and α-carboxyl groups of (5R)-5-hydroxy-L-lysine. The resulting 9-BBN complex was then employed in transformations such as N-Cbz protection, azido transfer, O-glycosylation, and O-silylation. Further manipulations led to improved methods for preparation of hydroxylysine and galactosylated hydroxylysine building blocks, suitable for direct use in peptide synthesis under standard Fmoc conditions.