(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid
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(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid

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Category
γ−Amino acids
Catalog number
BAT-007767
CAS number
72155-50-1
Molecular Formula
C11H15NO3
Molecular Weight
209.24
(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid
IUPAC Name
(3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid
Synonyms
AHPPA-OH; (3S,4S)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID; 3-HYDROXY-4-AMINO-5-PHENYLPENTANOIC ACID; L-threo-Pentonic acid,4-amino-2,4,5-trideoxy-5-phenyl-; (3S,4S)-Ahppa-OH; 4-amino-2,4,5-trideoxy-5-phenyl-L-threo-pentonic acid; AHPPA OH
Appearance
White solid
Purity
≥ 97%
Density
1.243±0.06 g/cm3 (Predicted)
Melting Point
97 °C
Boiling Point
452.0±45.0 °C (Predicted)
Storage
Store at -20 °C
InChI
InChI=1S/C11H15NO3/c12-9(10(13)7-11(14)15)6-8-4-2-1-3-5-8/h1-5,9-10,13H,6-7,12H2,(H,14,15)/t9-,10-/m0/s1
InChI Key
JAJQQUQHMLWDFB-UWVGGRQHSA-N
Canonical SMILES
C1=CC=C(C=C1)CC(C(CC(=O)O)O)N
1. Investigating the stereochemistry of binding to HIV-1 protease with inhibitors containing isomers of 4-amino-3-hydroxy-5-phenylpentanoic acid
B Raju, M S Deshpande Biochem Biophys Res Commun. 1991 Oct 15;180(1):187-90. doi: 10.1016/s0006-291x(05)81274-4.
A series of inhibitors containing all possible isomers of 4-amino-3-hydroxy-5-phenylpentanoic acid was synthesized and tested for inhibition of HIV-1 protease. Incorporation of the (3S,4S) isomer of the t-butyloxycarbonyl protected amino acid into the sequence Glu-Phe resulted in a potent inhibitor of HIV-1 protease (Ki = 63 nM). This inhibitor is at least 47-times more potent than the inhibitors containing other isomers of 4-amino-3-hydroxy-5-phenylpentanoic acid, indicating that the (3S,4S) isomer is the preferred isomer for binding to HIV-1 protease.
2. Inhibitors of human immunodeficiency virus type 1 protease containing 2-aminobenzyl-substituted 4-amino-3-hydroxy-5-phenylpentanoic acid: synthesis, activity, and oral bioavailability
P Lehr, A Billich, B Charpiot, P Ettmayer, D Scholz, B Rosenwirth, H Gstach J Med Chem. 1996 May 10;39(10):2060-7. doi: 10.1021/jm9508696.
Systematic modifications of HIV protease inhibitor (2R,3S,4S)-4-[[(benzyloxycarbonyl)-L-valyl]-amino]-3-hydroxy-2-[(4- methoxybenzyl)amino]-5-phenylpentanoyl)-L-valine 2-(aminomethyl)- benzimidazole amide led to a novel series of inhibitors with shortened, modified carboxy terminus. Their synthesis, in vitro enzyme inhibitory data, and antiviral activities are reported. Of particular interest are derivatives featuring the (1S,2R)-1-amino-2-hydroxyindan moiety at the P2'-position since some of them exhibit substantial oral bioavailability in mice. The influence of aqueous solubility and structural parameters on the oral resorption of the inhibitors is discussed. Optimum enhancement of oral bioavailability was observed with L-tert-leucine in P2-position, resulting in the discovery of (2R,3S,4S)-4-[[(benzyloxycarbonyl)-L-tert-leucyl]- amino]-3-hydroxy-2-[(4-methoxybenzyl)amino]-5-phenylpentanoic acid (1S,2R)-1-amino-2-hydroxyindan amide which combines high antiviral activity (IC50 = 250 nM) with a good pharmacokinetic profile (AUC = 82.5 microM.h at a dose of 125 mg/kg po in mice).
3. New potential renin inhibitors with dipeptide replacements in the molecule
Iwona Winiecka, Jadwiga Dudkiewicz-Wilczyńska, Iza Roman, Ryszard Paruszewski Acta Pol Pharm. 2010 Jul-Aug;67(4):367-74.
A series of eight non-peptidic potential renin inhibitors have been designed and synthesized. All of them contain dipeptide replacement: (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA) in their molecules. Four among them comprise two additional analogs of dipeptide: (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA) and (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (statine, Sta). All of the synthesized compounds contain also hydrophobic portions to receive a moderate lipophilicity of the molecules. Inhibitory activity of the compounds was measured in vitro by I-IPLC determination of Leu-Val-Tyr-Ser released from the N-acetyltetradecapeptide substrate by renin in the presence of the inhibitor. Asp-alpha(OEt)-(S,S)-ACHPA-epsilonAhx-Iaa (23) shows inhibitory activity (7%) at the concentration of 1.0 x 10(-2) M. The other synthesized compounds show no inhibitory activity up to this concentration.
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