190587-42-9

Basic information

• Product Name: N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester
• Synonyms: N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester
• CAS NO: 190587-42-9
• Molecular Weight: 854.01
• Mol File: 190587-42-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester(190587-42-9)
• EPA Substance Registry System: N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester(190587-42-9)

Safety Data

• Hazardous Substances Data: 190587-42-9(Hazardous Substances Data)

Upstream product

• 13574-13-5 Boc-Glu(OBzl)-OH 
• 147471-66-7 (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester 
• 127061-08-9 2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride 
• 190586-72-2 N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 56698-52-3 benzyl N-tert-butyloxycarbonyl-L-γ-glutamate α-N-methylamide 
• 82594-35-2 (S)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester 

Downstream Products

• 190587-46-3 (S)-4-Methylcarbamoyl-4-[(S)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester 
• 190587-47-4 (S)-4-[(S)-2-Amino-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-4-methylcarbamoyl-butyric acid benzyl ester 

Relevant articles and documents

Studies on selection blockers. 5. Design, synthesis, and biological profile of sialyl Lewis x mimetics based on modified serine-glutamic acid dipeptides.

We have rationally designed a sLe(x) mimetic based on molecular modeling, synthesized type II and type II' beta-turn dipeptides (3a,b), and evaluated their biological profiles both in vitro and in vivo. Against E-selectin-sLe(x) binding, the type II beta-turn dipeptide L-Ser-D-Glu 3a (IC50, 13 microM) and the type II' beta-turn dipeptide D-Ser-L-Glu 3b (IC50, 5.5 microM) were 20-100-fold more potent blockers than sLe(x) (1; IC50, 600 microM) and a 3'-sulfated Le(x) analog (2; IC50, 280 microM). On the other hand, other stereoisomers, such as L-Ser-L-Glu 3c and D-Ser-D-Glu 3d, were very weak blockers, with IC50 > 1000 microM for both 3c,d. Against the P- and L-selectins, despite much different stereochemistry of compounds 3a-d, the dipeptides 3a-d were all more potent blockers than either sLe(x) or compound 2. Interestingly, compound 3b provided significant in vivo efficacy against an immunoglobulin E-mediated skin reaction in a mouse model. These findings indicate that sLe(x) mimetics with type II and type II' beta-turn dipeptides could be useful in the design of an active selectin blocker in vitro and/or in vivo.