190586-78-8

Upstream product

• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 56698-52-3 benzyl N-tert-butyloxycarbonyl-L-γ-glutamate α-N-methylamide 
• 147471-66-7 (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 82594-35-2 (S)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester 

Downstream Products

• 190587-20-3 [N-(2-tetradecylhexadecanoyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-21-4 (S)-4-{(R)-2-Amino-3-[(2R,3S,4R,5R)-3,4-bis-benzyloxy-5-((S)-1-benzyloxy-ethyl)-tetrahydro-furan-2-yloxy]-propionylamino}-4-methylcarbamoyl-butyric acid benzyl ester 
• 1053633-94-5 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-61-2 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 216309-93-2 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-50-9 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-51-0 (S)-4-[(R)-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 
• 190587-03-2 [N-(tert-butoxycarbonyl)-O-(2,3,5-tri-O-benzyl-α-L-fucofuranosyl)-D-seryl]-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-44-1 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-57-6 -L-glutamic acid 1-methylamide 5-benzyl ester 

Relevant academic research and scientific papers

Fucose derivatives, drugs containing the same as active ingredient, and intermediates for producing the same

A compound of the formula (I): STR1 wherein X1 is a group of one of the following formulae (1), (2) and (3): STR2 R1 is a branched long chain alkyl group, R2 is --CONHR3, a carboxyl group or a hydrogen atom, n is an integer of 0, 1 or 2, and R3 is a lower alkyl group or a phenyl group, or a pharmaceutically acceptable salt thereof, which is useful as a selectin inhibitor, and can be used in the prophylaxis or treatment of various inflammatory diseases such as inflammatory dermatitis (e.g., atopic dermatitis, contact hypersensitivity, photodermatosis, etc.), autoimmune chronic diseases (e.g. rheumatoid arthritis, chronic thyroiditis, etc.), and ischemia-reperfusion injury.

Studies on selectin blockers. 6. Discovery of homologous fucose sugar unit necessary for E-selectin binding

We describe a mimic of the sugar unit of the E-selectin ligand, sialyl Lewis X (sLe(X)). Carbohydrates are entering the realm of rational drug design, aided by the growing understanding of the structure-function relationships. We investigated a new method

Studies on selectin blockers. 7. Structure-activity relationships of sialyl Lewis X mimetics based on modified ser-glu dipeptides

We have previously found that heterochiral fucodipeptides, L-Ser-D-Glu (3a) and D-Ser-L-Glu (3b), exhibited up to 20-100 times more potency than a sialyl Lewis X (sLe(X), 1) and a 3'sulfated Lewis X analogue (2) toward E- selectin binding and have also proposed, from molecular dynamics calculation, that their strong activities would depend on a possible formation of the type II and/or type II' β-turn of compounds 3a,b (Tsukida, T.; Hiramatsu, Y.; Tsujishita, H.; Kiyoi, T.; Yoshida, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534-3541). To clarify our hypothesis, we synthesized several analogues of compounds 3a,b and investigated their structure-activity relationships. As a result, it was indicated that the type II and/or type II' β-turn conformation would be a comparatively tight form and would play important roles in favorable binding to E-selectin. These findings indicate that sLe(X) mimetics with type II and type II' β-turn dipeptides could be a useful methodology for the design of an active selectin blocker.

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.