Chemoenzymatic synthesis of (1S,2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir

Demir, AS
Hamamcı, Haluk
Doganel, F
Ozgul, E
The synthesis of (1S,2R)-1-amino-2-indanol, a key component of HIV protease inhibitor is accomplished in four steps starting from indanone efficiently and with high levels of diastereo- and enantioselectivity. The starting material is converted into 2-acetoxy-1-indanone involving Manganese (III) acetate oxidation. The 2-acetoxyketone is hydrolyzed to 2-hydroxy-1-indanone enantioselectively using Rhizopus oryzae. Selective reduction of 2-hydroxyoxime derivative, derived from the 2-hydroxyketone, gives the amino alcohol up to 98% diastereo- and enantioselectivity. (C) 2000 Elsevier Science B.V. All lights reserved.


An efficient synthesis of (1S, 2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir
Demir, Ayhan Sıtkı; Aksoy-Cam, H; Camkerten, N; Hamamcı, Haluk; Doganel, F (2000-01-01)
(1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor is synthesized in four steps starting from indanone. The Mn(OAC)(3) mediated acetoxylation of indanone followed by fungus catalyzed hydrolysis of acetoxyindanone furnished optically pure alpha-hydroxy indanone. Formation and enantioselective reduction of oxime ether of 2-hydroxyindanone afforded (1S, 2R)-1-amino-2-indanol in 97% cis selectivity.
Thermodynamics and Kinetics of Association of Antibiotics with the Aminoglycoside Acetyltransferase (3)-IIIb, a Resistance-Causing Enzyme
Norris, Adrianne L.; Özen, Can; Serpersu, Engin H. (2010-05-18)
The thermodynamic and kinetic properties of interactions of antibiotics with the aminoglycoside acetyltransferase (3)-IIIb (AAC) are determined with several experimental methods. These data represent the first such characterization of an enzyme that modifies the 2-deoxystreptamine ring common to all aminoglycoside antibiotics. Antibiotic substrates For AAC include kanamycin A, kanamycin B, tobramycin, sisomicin, neomycin B, paromomycin, lividomycin A, and ribostamycin. Kinetic studies show that kanamycin gr...
Fungi mediated conversion of benzil to benzoin and hydrobenzoin
Demir, AS; Hamamcı, Haluk; Ayhan, P; Duygu, AN; Igdir, AC; Capanoglu, D (2004-08-23)
An enzyme system of four fungi catalyses the reduction of benzil to benzoin, as well as benzoin to hydrobenzoin. Depending on the pH of the medium, both enantiomers of benzoin can be obtained in good yield and high ee starting from benzil via a reduction, as well as from rac-benzoin via a novel deracemization reaction. Starting from benzil, (R)-, (S)- and rac-benzoin only (R,R)-hydrobenzoin was obtained in high ee and chemical yield.
Cytotoxic T Lymphocyte Activation Signals Modulate Cytoskeletal Dynamics and Mechanical Force Generation
Pathni, Aashli; Özçelikkale, Altuğ; Rey-Suarez, Ivan; Li, Lei; Davis, Scott; Rogers, Nate; Xiao, Zhengguo; Upadhyaya, Arpita (2022-03-01)
Cytotoxic T lymphocytes (CTLs) play an integral role in the adaptive immune response by killing infected cells. Antigen presenting cells (APCs), such as dendritic cells, present pathogenic peptides to the T cell receptor on the CTL surface and co-stimulatory signals required for complete activation. Activated CTLs secrete lytic granules containing enzymes that trigger target cell death at the CTL-target contact, also known as the immune synapse (IS). The actin and microtubule cytoskeletons are instrumental ...
Synthesis of peptide inhibitors for matrix metalloproteinase-2 and angiotensin converting enzyme /
Çiftçi, Burçe; Özçubukçu, Salih; Özen, Can; Department of Biotechnology (2014)
Matrix Metalloproteinases (MMPs) are one of the enzyme families of proteases that have zinc atom in the active site and they are involved in the degradation and regeneration of extracellular matrix. Specifically, they play an important role in tumor formation, tissue invasion, angiogenesis, and tumor metastasis. Matrix metalloprotease-2 (MMP-2) is a member of gelatinase class of MMP family and it has high activity in progression of skin, prostate, bladder, breast, lung, and ovary cancer. To control this inc...
Citation Formats
A. Demir, H. Hamamcı, F. Doganel, and E. Ozgul, “Chemoenzymatic synthesis of (1S,2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir,” JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, pp. 157–161, 2000, Accessed: 00, 2020. [Online]. Available: