56698-52-3

Basic information

• Product Name: Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(methylamino)-5-oxo-, phenylmethyl ester, (S)-
• CAS NO: 56698-52-3
• Molecular Formula: C18H26N2O5
• Molecular Weight: 350.415
• Mol File: 56698-52-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(methylamino)-5-oxo-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(methylamino)-5-oxo-, phenylmethyl ester, (S)-(56698-52-3)
• EPA Substance Registry System: Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(methylamino)-5-oxo-, phenylmethyl ester, (S)-(56698-52-3)

Safety Data

• Hazardous Substances Data: 56698-52-3(Hazardous Substances Data)

Upstream product

• 13574-13-5 Boc-Glu(OBzl)-OH 
• 541-41-3 chloroformic acid ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 593-51-1 methylamine hydrochloride 
• 74-89-5 methylamine 

Downstream Products

• 190586-78-8 N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 99764-63-3 Leu-Ser-p-nitro-Phe-Nle-Ala-Leu-OMe*TFA 
• 190586-72-2 N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 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 
• 190587-42-9 N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-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 
• 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 
• 211678-12-5 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 211678-14-7 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 211678-20-5 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 216309-87-4 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-57-6 -L-glutamic acid 1-methylamide 5-benzyl ester 

Relevant articles and documents

Synthesis and neuroprotective activity of analogues of glycyl-L-prolyl-L- glutamic acid (GPE) modified at the α-carboxylic acid

The synthesis of nine GPE* analogues, wherein the α-carboxylic acid group of glutamic acid has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-l-proline 2 with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE.

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.

Synthesis of Casein-Related Peptides and Phosphopeptides. I Solution-Phase Synthesis and 13C N.M.R. Spectroscopy of the Nα-Acetyl Octapeptide N-Methylamide Corresponding to Region 14-21 of Bovine β-Casein A2

The octapeptide, Ac-Glu-Ser-Leu-Ser-Ser-Ser-Glu-Glu-NHMe (1), was synthesized by the solution-phase method by using the mixed anhydride coupling procedure for the fragment condensation of the Nα-acetyl tripeptide, Ac-Glu(OBut)-Ser(But)-Leu-OH, with the pentapeptide N-methylamide hydrochloride, Cl*H2-Ser(But)-Ser(But)-Ser(But)-Glu(OBzl)-Glu(OBzl)-NHMe, followed by palladium-catalysed hydrogenolysis of Ac-Glu(OBut)-Ser(But)-Leu-Ser(But)-Ser(But)-Ser(But)-Glu(OBzl)-Glu(OBzl)-NHMe in trifluoroacetic acid.The synthesis of the two peptide fragments was accomplished in high yields and purity by using the repetitive excess mixed anhydride procedure and the isobutoxycarbonyl mixed anhydride of acetic acid for the rapid and high yielding N-acetylation of the tripeptide fragment. 13C n.m.r. spectroscopy was routinely used to monitor the efficiency of the coupling steps and to confirm the structure of octapeptide (1), signal assignments being possible for both the protected tri- and penta-peptides.