180509-18-6

Usage

Uses

Used in Medical Diagnostics:
2-(α-D-Mannopyranosyl)-L-tryptophan is used as a diagnostic tool for the accurate measurement of renal function. Its glycoconjugate nature enables it to be selectively taken up by the kidneys, providing a reliable and sensitive method for assessing kidney function and detecting any abnormalities or diseases related to the renal system.

Upstream product

• 252187-25-0 α-azido-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid 
• 65827-59-0 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 
• 74372-90-0 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose 
• 252187-19-2 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole 
• 252187-18-1 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-2-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole 
• 252187-21-6 α-azido-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole-3-propanoic acid 
• 252187-20-5 3-[(2S)-2-azido-3-hydroxypropyl]-1-(phenylsulfonyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole 
• 252187-17-0 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1-(phenylsulfonyl)-1H-indole 
• 252187-16-9 3-[(2S)-2-azido-3-[(tert-butyldimethylsilyl)oxy]propyl]-1H-indole 
• 154-09-6 L-tryptophanol 
• 358620-69-6 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester 
• 220339-91-3 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole 
• 220339-89-9 1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-2-o-(p-toluenesulfoamidyl)phenylethyne 
• 358620-68-5 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole 

Relevant academic research and scientific papers

Total synthesis of α-C-mannosyltryptophan, a naturally occurring C-glycosyl amino acid

A stereocontrolled synthesis of α-C-mannosyltryptophan, a new type of glycosyl amino acid, was achieved by Sc(ClO4)3 mediated coupling between α-C-mannosylindole and L-serine-derived 2-aziridinecarboxylate as a key step.

Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues

The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.

Total synthesis of mannosyl tryptophan and its derivatives

Glycosylation is one of the most important post- or co-translational modifications of proteins, which affects the biological activities of the parent proteins by influencing the higher-order structure. Recently, a highly novel variant of glycoproteins tha