@article { ISI:000232166800055, title = {Carbohydrate-based approach for the total synthesis of 1,3-polyol/alpha-pyrone antifungal natural products}, journal = {Journal of Organic Chemistry}, volume = {70}, number = {20}, year = {2005}, month = {SEP}, pages = {8216-8219}, publisher = {AMER CHEMICAL SOC}, type = {Article}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

An elimination and stereoselective hydrogenation of alpha-D-glucoheptonic-gamma-lactone derivative has been applied to prepare a differentially protected anti,anti-1,3,5-triol system, the utility of which has been extended for the total synthesis of anti-fungal 1,3-polyol/alpha-pyrone natural products.

}, issn = {0022-3263}, doi = {10.1021/jo050972v}, author = {Ramana, Chepuri V. and Srinivas, B. and Puranik, Vedavati G. and Gurjar, M. K.} } @article { ISI:000232860300043, title = {Chiral 2-C-methylene glycosides and carbohydrate-derived pyrano[2,3-b][1]benzopyrans: synthesis via InCl3 catalyzed stereoselective ferrier rearrangement of 2-C-acetoxymethyl glycal derivatives}, journal = {Tetrahedron Letters}, volume = {46}, number = {46}, year = {2005}, month = {NOV}, pages = {8047-8051}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

2-C-Acetoxymethyl glycal derivatives react with aliphatic alcohols in the presence of InCl3 (30 mol \%) to furnish the corresponding 2-C-methylene glycosides in excellent yields and with exclusive alpha-selectivity except for the methyl 2-C-methylene glycosides, which are formed in similar to 2:1 anomeric ratio in favour of the alpha-anomer. The reaction of 2-C-acetoxyglycals with phenols, however, produces the corresponding chiral carbohydrate-derived pyranobenzopyran derivatives via initial Ferrier rearrangement followed by tandem cyclization in excellent yields and moderate to high stereoselectivities in favour of the corresponding 10a-R-pyrano[2,3-b][1]benzopyran derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {2-C-methylene glycoside, InCl3, pyranobenzopyran, Stereoselective}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2005.09.059}, author = {Ghosh, R. and Chakraborty, A. and Maiti, D. K. and Puranik, Vedavati G.} } @article { ISI:000237886100006, title = {Convenient chemoenzymatic synthesis of (1S,7aS)-1-hydroxy-5-oxo-4-(2 {\textquoteleft}-carboxyethyl)-7a-methyltetrahydro-indane - a key intermediate of steroids}, journal = {Journal of Molecular Catalysis B-Enzymatic}, volume = {40}, number = {1-2}, year = {2006}, month = {MAY}, pages = {38-43}, publisher = {ELSEVIER SCIENCE BV}, type = {Article}, address = {PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS}, abstract = {

A porcine pancreatic lipase mediated enzymatic hydrolysis of (+/-)-1-acetoxy-5-oxo-4-(2 {\textquoteleft}-carbomethoxyethyl)-7a-methyltetrahydroindane (5b) furnished (1S,7aS)-1-acetoxy-5-oxo-4-(2 {\textquoteleft}-carbomethoxyethyl)-7a-methyltetrahydro-indane (9) and (1R,7aR)-1-hydroxy-5-oxo-4-(2 {\textquoteleft}-carbomethoxyethyl)-7a-methyltetrahydro-indane (8) with \> 99\% e.e. which on further chemical hydrolysis gave 1 and ent-1, key intermediates of steroids. (c) 2006 Elsevier B.V. All rights reserved.

}, keywords = {chemoenzymatic method, Enzymatic hydrolysis, steroids, terpenoids}, issn = {1381-1177}, doi = {10.1016/j.molcatb.2006.01.037}, author = {Kalkote, Uttam R. and Purude, A. N. and Puranik, Vedavati G. and Gurjar, M. K.} } @article { ISI:000250183300024, title = {Carbohydrate based approach towards the synthesis of aspercyclide C}, journal = {Tetrahedron Letter}, volume = {48}, number = {42}, year = {2007}, month = {OCT}, pages = {7524-7527}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A formal total synthesis of aspercyclide C (3) is described in which D-ribose is employed as a chiral pool material. The key step is a ring closing metathesis. (C) 2007 Elsevier Ltd. All rights reserved.

}, keywords = {chiron approach, D-ribose, Mukaiyama reagent, ring closing metathesis (RCM), Ullmann coupling}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2007.08.050}, author = {Ramana, C. V. and Mondal, Mohabul A. and Puranik, Vedavati G. and Gurjar, Mukund K.} } @article { ISI:000259799300016, title = {C-glycosides of dodecanoic acid: new capping/reducing agents for glyconanoparticle synthesis}, journal = {Tetrahedron Letters}, volume = {49}, number = {43}, year = {2008}, month = {OCT}, pages = {6227-6230}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A concise synthesis of 12-C-glycosylated dodecanoic acids employing an olefin cross-metathesis reaction is developed. Examination of these acids as capping agents for the synthesis of metal nanoparticles reveals that they do not cap the Co-metal nanoparticles synthesized in aqueous phase, but that two of them can reduce and cap the Ag nanoparticles in water without any aggregation. (C) 2008 Elsevier Ltd. All rights reserved.

}, keywords = {C-Glycosides, Cross metathesis, glyconanoparticles, Grubbs{\textquoteright} catalyst, silver nanoparticles}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2008.08.030}, author = {Ramana, C. V. and Durugkar, Kulbhushan A. and Puranik, Vedavati G. and Narute, Sachin B. and Bhagavatula L. V. Prasad} } @article { ISI:000259161600016, title = {Convenient access to 1, 3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation}, journal = {European Journal of Medicinal Chemistry}, volume = {43}, number = {8}, year = {2008}, month = {AUG}, pages = {1715-1720}, publisher = {ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER}, type = {Article}, address = {23 RUE LINOIS, 75724 PARIS, FRANCE}, abstract = {

Novel 1-aryl-3-(5-nitro-2-thienyl)-4-aroyl-pyrazoles 7 have been synthesized by the 1,3-dipolar cycloaddition of 3-arylsydnones 3 with 1-aryl-3-(5-nitro-2-thienyl)-2-propyn- 1-ones 6. The newly synthesized compounds were well characterized by elemental analysis, IR, (1)H NMR and mass spectral studies. They were also screened for their antibacterial and antifungal activities against a variety of microorganisms and the results of such studies have been discussed in this article. (c) 2007 Elsevier Masson SAS. All fights reserved.

}, keywords = {1, 3-dipolar cycloaddition, 5-nitrothiophene, acetylenic ketone, Antibacterial, antifungal, Pyrazole, sydnone}, issn = {0223-5234}, doi = {10.1016/j.ejmech.2007.08.002}, author = {Rai, N. Satheesha and Kalluraya, Balakrishna and Lingappa, B. and Shenoy, Shaliny and Puranik, Vedavati G.} } @article { ISI:000268231500057, title = {Combinatorial library of primaryalkylammonium dicarboxylate gelators: a supramolecular synthon approach}, journal = {Langmuir}, volume = {25}, number = {15}, year = {2009}, month = {AUG}, pages = {8742-8750}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

Following the supramolecular synthon approach, a combinatorial library comprising 35 organic salts derived from 7 dicarboxylic acids (malonic, succinic-, adipic, L-tartaric-, maleic-, phthalic-, and isophthalicacid) and 5 primaryalkyl amines Me-(CH2)(n)-NH2 (n = 11 - 15) was prepared and scanned for gelation. About 66\% of the salts in the combinatorial library were found to show moderate to good gelling ability in various polar and nonpolar solvents including commercial fuels such as petrol. The majority of the salts having a rigid, unsaturated anionic backbone (maleate, phthalate, and isophthalate) did not show gelation; only the corresponding hexadecylammonium salts showed gelation. Some of the representative gels were characterized by rheology, small-angle neutron scattering (SANS), optical microscopy (OM), and scanning electron microscopy (SEM). Single-crystal structures of two gelator and two nongelator salts were also discussed in the context of supramolecular synthon and structure-property correlation.

}, issn = {0743-7463}, doi = {10.1021/la9001362}, author = {Sahoo, Pathik and Adarsh, N. N. and Chacko, George E. and Raghavan, Srinivasa R. and Puranik, Vedavati G. and Dastidar, Parthasarathi} } @article { ISI:000285749800008, title = {Conformationally rigid aromatic amino acids as potential building blocks for abiotic foldamers}, journal = {Organic \& Biomolecular Chemistry}, volume = {9}, number = {2}, year = {2011}, month = {NOV}, pages = {367-369}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

This communication describes the development of conformationally constrained unnatural aromatic amino acids, constructed on rigid backbone wherein the carboxyl and amino groups project in two dimensions (planes) on the aromatic framework. Such a feature offers the possibility of design and development of conformationally ordered synthetic oligomers with intriguing structural architectures distinct from those classically observed. Furthermore, such amino acids will have the potential to extend the conformational space available for foldamer design with diverse backbone conformation and structural architectures.

}, issn = {1477-0520}, doi = {10.1039/c0ob00593b}, author = {Ramesh, Veera V. E. and Roy, Arup and Vijayadas, Kuruppanthara N. and Kendhale, Amol M. and Prabhakaran, Panchami and Gonnade, Rajesh G. and Puranik, Vedavati G. and Sanjayan, Gangadhar J.} } @article { ISI:000310863400012, title = {Carbohydrate-derived conformationally restricted bicyclic dipeptides as potential hetero foldamer building blocks}, journal = {Tetrahedron-Asymmetry}, volume = {23}, number = {18-19}, year = {2012}, month = {OCT}, pages = {1400-1404}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Starting from carbohydrate precursors, hetero foldamer building blocks featuring diverse amino acid side chains and stereochemistry have been accessed via a multi-step synthetic protocol. These conformationally restricted bicyclic dipeptide building blocks are characterized by a constrained beta-lactam ring fused with a pyrrolidine ring carrying a hydroxyethylamine isostere (HEA) on the backbone. These building blocks offer the possibility of developing foldamers with interesting structural architectures, conspicuously different from those classically observed. Furthermore, such hetero-building blocks have the potential to augment the conformational space available for foldamer design with diverse backbone conformations and structural architectures. (C) 2012 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2012.08.007}, author = {Ramesh, Veera V. E. and Puranik, Vedavati G. and Sanjayan, Gangadhar J.} } @article { ISI:000317327900022, title = {Carboxamide versus sulfonamide in peptide backbone folding: a case study with a hetero foldamer}, journal = {Organic Letters}, volume = {15}, number = {7}, year = {2013}, month = {APR}, pages = {1504-1507}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

Strikingly dissimilar hydrogen-bonding patterns have been observed for two sets of closely similar hetero foldamers containing carboxamide and sulfonamides at regular intervals. Although both foldamers maintain conformational ordering, the hydrogen-bonding pattern and backbone helical handedness differ diametrically.

}, issn = {1523-7060}, doi = {10.1021/ol4002762}, author = {Ramesh, Veera V. E. and Kale, Sangram S. and Kotmale, Amol S. and Gawade, Rupesh L. and Puranik, Vedavati G. and Rajamohanan, P. R. and Sanjayan, Gangadhar J.} } @article { ISI:000331895900018, title = {Conformational modulation of peptide secondary structures using beta-aminobenzenesulfonic acid}, journal = {Chemical Communications}, volume = {50}, number = {22}, year = {2014}, month = {JAN}, pages = {2886-2888}, publisher = {ROYAL SOC CHEMISTRY}, type = {Article}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

This communication describes the influence of beta-aminobenzenesulfonic acid ((S)Ant) on the conformational preferences of hetero foldamers. The designed (Aib-(S)Ant-Aib)(n) and (Aib-(S)Ant-Pro)(n) oligomers display a well-defined folded conformation featuring intramolecular mixed hydrogen bonding (7/11) and intra-residual (6/5) H-bonding interactions, respectively.

}, issn = {1359-7345}, doi = {10.1039/c3cc48850k}, author = {Kale, Sangram S. and Kunjir, Shrikant M. and Gawade, Rupesh L. and Puranik, Vedavati G. and Rajamohanan, P. R. and Sanjayan, Gangadhar J.} } @article { ISI:000329886900036, title = {Cu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical}, journal = {New Journal of Chemistry}, volume = {38}, number = {1}, year = {2014}, month = {JAN}, pages = {277-284}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

1,1{\textquoteright}-Methide-bi-vitamin K-3 (B) has been isolated as a dinaphthoquinone methide radical (DNQM) by the transformation of 1-imino(acetylhydrazino)-vitamin K-3 (A). The transformation follows a biomimetic activation pathway mediated via Cu(II) ion catalyzed oxidative coupling. Single crystal X-ray and electron spin resonance (ESR) experiments combined with density functional calculations elucidate the {\textquoteleft}{\textquoteleft}resonance structure{\textquoteright}{\textquoteright} of the DNQM radical (B). Fluorescence investigations reveal that DNQM facilitates interaction with the cysteine residue. As compared to the parent substrate, B shows a depletion in the level of GSH, triggering apoptosis in HeLa cells.

}, issn = {1144-0546}, doi = {10.1039/c3nj00783a}, author = {Badave, Kirti D. and Patil, Shalaka S. and Khan, Ayesha A. and Srinivas, Darbha and Butcher, Raymond J. and Gonnade, Rajesh G. and Puranik, Vedavati G. and Pinjari, Rahul V. and Gejji, Shridhar P. and Rane, Sandhya Y.} } @article { ISI:000349401300020, title = {Conformational modulation of peptides using beta-amino benzenesulfonic acid ((S)Ant)}, journal = {Organic \& Biomolecular Chemistry}, volume = {13}, number = {7}, year = {2015}, month = {DEC}, pages = {2087-2091}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

This communication describes the utility of a conformationally restricted aromatic beta-amino acid (2-aminobenzenesulfonic acid, (S)Ant) inducing various folding interactions in short peptides. Sandwiching (S)Ant between diverse amino acid residues was shown to form robust folded architectures featuring a variety of H-bonded networks, suggesting its utility in inducing peptide folding.

}, issn = {1477-0520}, doi = {10.1039/c4ob02421d}, author = {Priya, Gowri and Kotmale, Amol S. and Chakravarty, Debamitra K. and Puranik, Vedavati G. and Rajamohanan, Pattuparambil R. and Sanjayan, Gangadhar J.} } @article { ISI:000368941700025, title = {Comparative study of dG affinity vs. DNA methylation modulating properties of side chain derivatives of procainamide: insight into its DNA hypomethylating effect}, journal = {RSC Advances}, volume = {6}, number = {7}, year = {2016}, month = {JAN}, pages = {5350-5358}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

Procainamide derivatives have been synthesized to investigate the role of side chains in modulating the DNA methylation level in cancer cells and gain insight into its mechanism of action. The synthesized derivatives comprised of flexible (dimethyl), constrained (pyrrolidine, piperidine, morpholine) and planar aromatic (pyridine, phenyl) side chain motifs. The affinity of procainamide and its derivatives towards the deoxyguanosine (dG) base in neutral form has been assessed by performing Differential Pulse Voltammetry (DPV) under physiological conditions. Further, molecular docking with hemimethylated CpG rich DNA acquired from an active mDNMT-1-DNA (PDB ID-4DA4) crystal structure, reveals their preferential non-covalent interaction with dG nucleobase in the intercalation cavity of the minor groove. Differential affinity of the derivatives to dG base in neutral and bound forms (DNA) is correlated with their DNA methylation modulating properties at sub-lethal concentrations. Among all the derivatives, a compound with an aromatic phenyl side chain (1) has shown a highest binding affinity for dG nucleobase in neutral form as well as for partially denatured CpG rich DNA which is attributed to the formation of p/p stacking interaction in addition to N-H/O hydrogen bonding with the pyrimidine ring of dG base. It also shows the highest cytotoxicity and global hypomethylation at a sub-lethal level in the MCF-7 cancer cell line compared to other derivatives and procainamide. A docking study has also illustrated the plausible structural basis of DNA methylation modulating a property of procainamide. Strong association of procainamide with dG bases of partially denatured CpG rich DNA via H-bonding and other non-covalent interactions may alter the active topology of DNA required by the DNA-binding regulatory proteins (e. g. DNMT-1) which is validated by a DNMT-1 inhibition assay. This systematic investigation leads to a new potent alternative to procainamide being found and gives a plausible insight into the DNA hypomethylating effect of procainamide.

}, issn = {2046-2069}, doi = {10.1039/c5ra20012a}, author = {Gawade, Rupesh L. and Chakravarty, Debamitra K. and Debgupta, Joyashish and Sangtani, E. and Narwade, S. and Gonnade, Rajesh G. and Puranik, Vedavati G. and Deobagkar, D. D.} }