Curriculum Vitae
`RAMAIAH MUTHYALA
`
`Home address:
`699 Apache Lane
`Mendota Heights, MN 55120
`Ph: 651 688 7382, 612-202-6168
`
`Office address:
`College of Pharmacy,
`Department of Experimental Clinical Pharmacology
`717 Delaware SE, Room 460
`University of Minnesota, \Minneapolis, MN 55120
`612-624-7120, Fax: 612-626 2595
`Email: muthy003@umn.edu
`
`I. EDUCATION
`Ph.D., Heterocyclic Chemistry - University of East Anglia, UK (1975)
`Ph.D., Natural Products - Sagar University, India (1970)
`M.B.A., International Management (MIM) - St. Thomas University, MN (1999)
`M.P.H., Public Health Practice – University of Minnesota, MN (2017
`expected)
`II. ACADEMIC EXPERIENCE
`UNIVERSITY OF MINNESOTA
`Associate Professor, Department of Experimental Clinical Pharmacology
`(August 2006-)
`Adjunct Associate Professor, Department of Medicine (March, 2005 - )
`Associate Professor, Department of Medicinal Chemistry (August. 2000 -
`2007)
`Associate Director (pre-clinical drug development), Center for Orphan Drug
`Research (July 2005 - 2009)
`Senior Associate Director, Center for Drug Design (Aug. 2000 - June 2005)
`Research activities: Anti-HIV drugs (integrase, protease and reverse
`transcriptase inhibitors); Antibiotics for multi-drug resistant strains;
`Vancomycin mimics (VanX inhibitors, efflux inhibitors); Alzheimer's Disease
`(-secretase inhibitors, prodrugs to cross blood-brain barrier); Rare
`cancers (Hemangioblastoma, biliary tract carcinoma); Rare neurological
`diseases (Spinocerebellar ataxia type-1, Rett syndrome); Rare
`hemoglobinopathies (Sickle cell anemia, thalassemia); Rare antibiotic
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`resistant bacterial infections; Synthetic methods development leading to
`bioactive natural products; Combinatorial chemistry (heterocyclic compound
`libraries for HTS); Molecular modeling; Assay development; high
`throughput screening of NIH compound libraries; Pharmacokinetic
`concepts, discovery of quality clinical candidates, repositioning of FDA
`approved drugs for orphan diseases.
`Teaching: Foundations of Critical Thinking (FCT) , Medical School, University
`of Minneosta; Fundamentals of Medicinal Chemistry; Heterocyclic
`Chemistry; Synthetic Organic Chemistry; Orphan Drug Development – one
`day course for pharma industry, Short course (Orphan Drug Development
`through Repositioning) at American Association of Pharmaceutical
`Sciences.
`Administrative responsibilities: Primary advisor to the CDD director
`regarding overall research, management and operation of the Center.
`Responsibilities included program development, supervision, policymaking,
`and budget preparation, hiring personnel, organizing national and
`international conferences, procurement of lab instrumentation and
`equipment, renovation and maintenance of labs, and advising the director
`on budgetary and related issues; Preclinical studies, phase 1 clinical trials
`coordinator (NDA approved projects).
`NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION &
`RESEARCH, Hyderabad, AP India, Adjunct Professor, 2016-
`ALZHEIMER'S RESEARCH CENTER, Regions Hospital, St. Paul, MN,
`Research Associate (1999-2000):
`Isolation and characterization of endogenous inhibitor for mAChR from
`brains of Alzheimer’s patients; Mechanism of free radical inactivation of
`mAChR; SAR of Anandamide Analogues; Combinatorial Chemistry;
`Molecular modeling of mAChR; Substrate specific -Secretase inhibitors;
`Synthesis of naturally occurring antioxidants.
`UNIVERSITY OF DELHI, INDIA
`Visiting Professor, Ambedkar Biomedical Research Institute (Jan 2003 -)
`Adjunct Professor, Andhra University, Vishakapatnam, AP, India (Sept
`2015)
`EASTERN MICHIGAN UNIVERSITY, Ypsilanti, MI
`Adjunct Professor (1984-1989): Graduate Research Advisor; taught
`advanced organic chemistry course: asymmetric synthesis, synthetic
`strategies for total synthesis of complex natural products, synthetic
`methodologies.
`POSTDOCTORAL EXPERIENCE
`Wayne State University, Detroit, MI (1974-1976)
`Total synthesis of natural products and novel synthetic methodologie.
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`University of North Wales, Bangor, U.K (1971-1972)
`Enzymatic degradation and structure elucidation of sea weed constituent,
`Algenic acid
`Osmania University, Hyderabad, India (1970-1971)
`Synthesis of new sulfur and nitrogen heterocyclic compounds for Human
`Anti-parasitic diseases; anti-malarial, anti-tuberculosis
`National Chemical Laboratory, Poona, India (1969-1970)
`Isolation and characterization of biologically actives coumarins,
`isocoumarines, poly phenolic compounds (Gossypol type) from medicinal
`plants
`III. INDUSTRIAL EXPERIENCE
`3M/IMATION CORPORATION, St. Paul, MN
`Senior Research Specialist, Medical Imaging Technology Center (1989-
`1999)
`Project and program management: Responsible for development of medical
`imaging diagnostic materials (synthesis and structure, activity relationships
`of infrared dyes); photo dynamic therapy, using tumor specific dyes;
`combinatorial chemistry (dyes); SAR; computational chemistry and
`molecular modeling using semi-empirical quantum mechanical and ab intio
`methods; Mopac, Gaussian and other computational software. Taught the
`use and application of CAChe software (Computer-Aided Chemistry) to
`bench chemists, 2D NMR quantitative structure analysis;
`DOW CHEMICAL COMPANY, Midland, MI
`Project Leader, Pharmaceuticals Research & Development (1979-1989)
`Project coordinator/manager - Design and synthesis of enzyme inhibitors
`(suicide-enzyme inactivators, pyridoxal-5'-phosphate dependent enzyme
`inhibitors, transamination of
`- amino acids, decarboxylation of -
`, a n d 
`amino acids, amine oxidations, and racimization of L-and D-amino acids);
`new and alternate synthesis for anti-allergy and cardiotonic drugs;
`practical synthesis of (+) vinylGABA (anti-epileptic) and difluoromethyl
`ornithine, DFMO (sleeping sickness) without resolution; kilo synthesis of
`fluoro amino acids for FDA approval; identification and synthesis of
`metabolites. Biotechnology - chemical modification of proteins, radioactive
`metal complexes and monoclonal antibodies for cancer diagnosis and
`therapy; develop GMP guidelines and work with government regulators;
`analytical support, enhanced training in 2D NMR; Technical project
`management and supervision of MS. PhD and other technical employees
`SCHERING PLOUGH, Bloomfield, NJ
`Research Associate, Infectious diseases department (1976-1979)
`Synthesis of antibiotics and antifungal agents; Aminoglycosides:
`modification of gentamicin type antibiotics to reduce toxicity (muscular
`dystrophy); HMGA-CoA reductase inhibitors: Cerulenin and its
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`carbocerulenin anologues as fatty acid synthase inhibitors (breast
`cancer), diphenylethers, (-lactam antibiotics. Structure activity
`relationships using CODESSA; New synthetic methods - allyloxycarbonyl
`functionality for the protection of amines and carboxylic acids and
`deprotection with Pd; One pot multi-step reactions for gram to kilogram
`quantity reactions
`INDIAN DRUGS & PHARMACEUTICALS LTD, Hyderabad, India
`Senior Chemist, Process Control & Process Development
`laboratory (1969-1971)
`Laboratory head for quality control, process and pilot plant
`laboratories - Manufacture of analgesics, sulfa-drugs and
`vitamins.
`COMMERCIAL SUCCESS
`(s)Vinyl-GABA (Vigabatrin A gaba tranaminase inhibitor). Antiepileptic (used for
`refractory complex partial seizures); under development in U.S. as an orphan
`drug (approved), it is available in many countries around the world for the
`treatment of epilepsy and infantile spasms. Prevents the biochemical and
`behavioral effects of alcohol, nicotine and cocaine in much the same way it
`prevents an epileptic seizure: by altering the way brain cells communicate to
`one another (Marion-Merrill-Dow).
`α-Difluoromethyl Ornithine (DFMO, Diflore) Suicide inhibitors technology was
`originated at Merrill Research Center, Strasburg, France. DFMO, an enzyme-
`activated, irreversible inhibitor of ornithine decarboxylase, blocks polyamine
`biosynthesis and has anti-tumor effects in animal tumor models as well as in
`athymic mice implanted with human small cell carcinoma; reduces in vitro
`invasiveness and metastatic capacity of some breast cancer cells. Eventually
`this product was sold to the World Health Organization to treat one of the
`neglected diseases, African sleeping sickness (Trypanosomiasis) (Marion-
`Merrill-Dow).
`Radiolabeled biopharmaceuticals: Tumor targeting with monoclonal antibody
`(MAb) with cancer-killing radioisotope technology. Radioisotope I-131 for rare
`thyroid cancer treatment; yittrium-90 for ovarian cancer are a few among the
`short lived radioisotopes investigated Complementary to monoclonal antibody
`as target identifiers, stable complexes of radioisotopes with organic small
`molecule complexing agents (MeO-DOTA) which link with target protein to
`deliver the cancer-killing payload precisely where it is most needed were also
`developed. Dow set up a new business, ChelaMed Radiopharmaceutical
`Services, based on this technology (Dow Chemicals).
`Allyloxy carbonyl protecting group for amines and alcohols and their applications
`to amino glycoside and beta lactam antibiotics were developed (only one
`author). This idea was further extended for other functional groups e.g.,
`carboxylic acids by academic and industrial scientists (Schering-Plough).
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`Medical imaging technology: novel functional dyes (diagnostic and treatment)
`which were developed using predictive power of computational methods. The
`resulting business, Dry Silver, was sold to Imation and eventually to Kodak-
`Asai (3M Company).
`Highlights from the University of Minnesota website:
`http://www1.umn.edu/umnnews/Feature_Stories/Propolis_an_ancient_remedy
`_may_fight_AIDS.html
`http://www1.umn.edu/umnnews/Feature_Stories/The_emerging_uses_of_bioc
`atalysis.html
`http://www1.umn.edu/umnnews/Feature_Stories/Beauty_in_the_hive_of_the_
`beholder.html
`IV. LEADERSHIP
`• Member of the Executive Board of Directors, Vorin Laboratories, India;
`• Consultant to Ranbaxy, New Delhi, India (1994-1998)
`• Member of the Executive Board of Directors, Suven LifeSciences, India,
`(1996 –2005)
`• Member of the Editorial Board of ARKAT Foundation, Gainesville, FL (1999
`- present)
`• Co-chair, Working Group on Chemically-derived products including
`repurposing; Therapies Scientific Committee, International Rare Diseases
`Research Consortium 2014-
`• NIH Drug Discovery for the Nervous System program review panel (2012-
`present
`• NIH Molecular Libraries and Imaging Roadmap initiative: Molecular Libraries
`Probe Production Centers (MLPCN) Evaluator, 2010-present
`Founding Member of the Board of Directors, In Need of Diagnosis Inc.
`Orlando, FL (2006 -2008)
`• Founder, President, Indian Organization for Rare Diseases, 2005-
`
`V. PROFESSIONAL INVOLVEMENT (selected)
`• Organizer for “raising the awareness of rare diseases” A national conference
`at Hyderabad, Telangana, India (March 20, 2015)
`• Organizer for “Therapeutics for Rare and Neglected Diseases” at Central Drug
`Research Institute, Lucknow, India (World Rare Diseases Day, Feb 26-8,
`2013)
`• Guest of Honor to Innova Children’s Heart Hospital, Hyderabad, India, to
`address graduating students of nursing and other hospital technologies.(Nov
`26, 2011)
`• Planning committee member of the iDDi workshop on Neglected and Orphan
`diseases, Siena, Italy, May29-June1, 2010
`• Organizer, symposium – Medicinal Chemistry in Rare, Orphan and neglected
`Diseases; 239th ACS National Meeting, San Francisco, CA, March 21-25,
`2010
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`• Organizer symposium - Discovery Research Program on Orphan Diseases -
`An Indo- US Bilateral Workshop Sponsored by the Indo- US Science and
`Technology Forum, New Delhi, India; University of Minnesota, April 26-29,
`2009
`• Session chair/organizer: Orphan drug discovery and development, AAPS
`annual meeting, San Diego, California, October 11-15, 2007
`• AAPS Emerging Regulatory Guidance Task Force, Drug Discovery and
`Development section representative 2006-7
`• Session Chair/Speaker: 2nd International Symposium on Green/Sustainable
`Chemistry: January 10-13, 2006, Delhi, India
`• Session Chair/Speaker: Organic Processes and Natural Products
`Synthesis: An International Symposium, April 1-3, 2005, Hyderabad, India
`• Organization Secretary/Speaker: Chemistry Biology Interface: Synergistic
`New Frontiers Symposium; Nov 21-26, 2004, New Delhi, India
`• Organizer/Chairperson/Speaker, Florida Heterocyclic conferences,
`University of Florida, Gainesville, Fl, USA, 2001-
`• Editor, Contributing: Highlights, Organic Process Research and
`Development, Pub: American Chemical Society (2005-06)
`• Editor, Contributing: HeartCuts, ChemTech - Pub: American Chemical Society
`(1997 - 2003)
`• Scientific editor – commemorative issue in honor of Dr. A.V. Rama Rao,
`Archive for Organic Chemistry (2005)
`• Editor, Chemistry and Applications of Leuco Dyes (book, Plenum Press, New
`York (1997)
`• Editor, Midland Chemist, American Chemical Society Publication (1983-89)
`• Technical Editor, ARKIVOC a new electronic chemistry journal (1999-2003)
`• Scientific Editor, ARKIVOC a new electronic chemistry journal (2004-present)
`• Editor, Mini-Reviews in Medicinal Chemistry, published by Bantam Science (2009 -
`• Organizer and host, XVI International Roundtable Conference,
`Nucleosides, Nucleotides and Nucleic acids; Minneapolis, Minnesota, USA
`2004
`• Organizer/Coordinator, USA: The Millennium 52nd Indian Pharmaceutical
`Congress, Hyderabad, India: A symposium on Alzheimer’s and Related
`Diseases, Nov.30-Dec.3, 2002
`VI. HONORS AND AWARDS:
`• Recipient of “S.C.Amita Award” from Indian Chemical Society, (2006)
`• Elected to Fellow of Royal Society of Chemistry (FRSC) (2001)
`VII. PROFESSIONAL ASSOCIATIONS:
`• Royal Society of Chemistry
`• American Chemical Society
`• International Society for Antiviral Research
`• American Society of Pharmacognosy
`• International Society of Nucleosides, Nucleotides, and Nucleic acids
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`• American Association of Pharmaceutical Scientists
`VIII. INVITED LECTURS (Recent):
`• World Orphan Drug Congress, Washington DC, April 23-25, 2014
`• Drug Discovery Summit, Boston, May 8-10, 2013
`• Pharmaceutical Export Promotion Council of India, Annual General body
`meeting, Hyderabad, India, 24-25, 2013
`• World Drug Repositioning Congress, London, UK Sept 13, 2012
`• Drug Repositioning & Indications: Discovery Conference, San Francisco, Oct
`24,2012
`• AstraZeneca, Bangalore, India March 19, 2011
`• BITS Pilani, Rajastan, India, April 1, 2011
`• All India Institute of Medical Sciences, New Delhi, India, 04/3/2011
`• Plenary lecture at the international conference on ‘Bridging gaps in discovery
`and development: Chemical & Biological Sciences for Affordable Health,
`Wellness & Sustainability’ organized by the Indian Society of Chemists and
`Biologists’; at Saurashtra University, Rajkot, Gujarat. Feb 6, 2011
`• Guest of Honor at the Silver Jubilee Celebrations of Sri Devaraj Urs Academy
`of Higher Education and Research, Kolar, Bangalore (Karnataka) Feb 8,
`2011
`• The Indian Institute of Technology (IIT) Bombay, Feb 9, 2011
`• iDDi Workshop on Neglected and Orphan Diseases, Siena, Italy May 29-June
`1, 2010
`• The interface of chemistry biology in biomedical research; BITS, Pilani,
`Rajasthan, India. Feb 22-25, 2008
`• 2nd Annual Drug Repositioning Summit, Philadelphia, PA, September 10-
`11, 2007
`• SC Ameta Award lecture, Indian Chemical Society, Annual meeting,
`Aurangabad, India, December 25, 2006,
`• 1st World Congress, Association for Prudent Use of Antibiotics, Boston,
`December 11, 2006,
`• 232nd National meeting, American Chemical Society, San Francisco,
`(Spotlight paper, Med.Chem. Section) September 13, 2006,
`• NORD annual conference with NIH Office of Rare Diseases, Washington
`D.C. October 1, 2005,
`IX. EXTERNAL Ph.D. THESIS EXAMINER (recent 2004 - )
`Studies on the interaction of various anti-cancer drugs with a promoter region of
`c-METproto-oncogene and the effect of these drugs on MET expression in
`Hepatoma - All India Institute of Medical Sciences (AIIMS), New Delhi, April
`2010
`Design, Synthesis and Biological Evaluation of New Pyrrolo[2,1-
`c][benzodiazepines as Antimitotic and Anticancer Agents - Acharya
`Nagarjuna University, Nagarjuna Nagar, India. May 2009
`Towards the total synthesis of antitumor agents (+) and (-)Altholactone, (+) and
`(-) Isoaltholactone, (+) and (-) Goniothales diol and Petrosynol – University
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`of Pune, and Indian Institute of Chemical Technology, Hyderabad, India,
`January 2007
`Studies Directed Towards Total Synthesis of Constanolactone A, B and
`Development of Novel Synthetic Methodologies – Sri Venkateswara
`University, Tirupathi, and Indian Institute of Chemical technology,
`Hyderabad, India, April 2006
`Synthesis and Biological Activity Studies of New Fused Heterocycles Containing
`Two Sulphur Atoms – National Institute of Technology, Warangal, India,
`March 2005
`Synthesis and Biological Activity Studies of Novel Types of Oxygen and Sulphur
`Containing Fused Heterocycles - National Institute of Technology, Warangal,
`India, February 2005
`Synthesis of Biologically Active Compounds and Development of New
`Methodologies – University of Kalyani, W. Bengal, India, February 2004
`X. JOURNAL REVIEWER
`Journal of Organic Chemistry
`Journal of Medicinal Chemistry
`Tetrahedron Letters
`Bioorganic and Medicinal Chemistry
`Journal of Alternative and Complementary Medicine
`Journal of Ethanopharmacology
`Journal of Heterocyclic Chemistry
`Heterocycles
`Synthesis
`Organic Preparative Procedures International
`Journal of Molecular Catalysis A: Chemical
`DNA and Cell Biology
`Cancer Investigation
`ARKIVOC
`Synthetic Communication
`Organic and Medicinal Chemistry Letters
`XI. RESEARCH GRANT REVIEW STUDY SECTIONS
`• Faculty Development Grants – Academic Health Center, University of
`Minnesota (2002-2003)
`• US NIH Drug Discovery for the Central Nervous System program review
`panel (2012-present
`• US NIH Molecular Libraries and Imaging Roadmap initiative: Molecular
`Libraries Probe Production Centers (MLPCN) Evaluator, 2010-present
`• Undergraduate Research Opportunities Program Scholarships – University of
`Minnesota 2011-
`• Health Research Council of New Zealand 2012-
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`• European Union Funding for Research and Innovation–ERC Consolidated
`grants, Belgium (2012)
`
`XII PUBLICATIONS (selected)
`
`Ramaiah Muthyala, Shin WS, Xie J, Sham YY, Discovery of 1-hydroxypyridine-2-
`thiones as selective histone deacetylase inhibitors and their potential
`application for treating leukemia, Bioorganic Med. Chem.Lett. 25(19), 2015,
`4320-4
`Ramaiah Muthyala, Namrata Rastogi, Woo Shik Shin, Marnie L. Peterson, and Yuk
`Yin Sham; Cell permeable vanX inhibitors as vancomycin re-sensitizing
`agents; Bioorganic Medicinal Chemistry Letters, 24 (2014) 2535-2538
`Ramaiah Muthyala, Orphan/Rare drug discovery through drug repurposing Ed. Chris
`Lipinski, :”Drug Repurposing”; Drug Discovery Today, 2011, 8, 3-4, p71-76
`“Synthesis and Applications of Leuco Dyes” (Chinese) Editor: R. Muthyala, Springer,
`Netherlands (2011)
`Srinivas Rao, Yaragorla and Ramaiah Muthyala; Concise Total Synthesis of
`Cytotoxic Natural Products (+) and (-)-muricatacin;. ARKIVOC, 2010, X, p178-
`184
`Srinivasarao Yaragorla and Ramaiah Muthyala; Formal total synthesis of (-)-balanol:
`a potent PKC inhibitor, Tetrahedron Letters, 2009, 51, 467-470.
`Lin, Y.C., Schlievert, P.M., Anderson, M. J., Fair, C. L., Schaefers, M.M., Muthyala,
`R., Peterson, M.L., Glycerol monolaurate and dodecylglycerol effects on
`Staphylococcus aureus and toxic shock syndrome toxin-1 in vitro and in vivo -
`PLoS One. 2009 Oct 19;4(10):e7499.; PMID: 19838303
`Ye Tang, Ramaiah Muthyala and Robert Vince, Synthesis and biological evaluation
`of carboacyclic nucleosides with (Z) and (E)-9-[4,4-bis(hydroxymethyl)]-2-
`butenyl side chain Bioorganic Medicinal Chemistry, (2006), 14(17), 5866-
`5875; PMID: 16759867
`Ramaiah Muthyala and A. Venkateswarlu: Medicinal Chemistry in India: Express
`Pharma Pulse, (India's No.1 Weekly for the Pharmaceutical Industry) 9th June
`2005, and 16th June 2005:
`http://www.expresspharmapulse.com/20050609/drugdevelopment01.shtml
`http://www.expresspharmapulse.com/20050616/drugdevelopment01.shtml
`Muthyala Ramaiah; Vince, Robert; Vinyl- and arylmetals. “Comprehensive Organic
`Functional Group Transformations II” Ed: Katritzky, Alan; Taylor, Richard,
`(2005), 2 1025-1057
`R. Muthyala, “Comprehensive Organic Functional Group Transformations” Eds.
`Christopher Moody, (1995) 5, 1061-89
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`M. Ramaiah, Free Radical Reactions in Organic Synthesis. Tetrahedron, 37, 3541,
`(1987)
`M. Ramaiah, and T. L. Nagabhushan,Synthesis of Carbacerulenin: A General
`Method for Synthesis of E,E-1,4-Dienols. Synthetic Communications, 1986,
`16, 1049
`M. Ramaiah, A New Convenient Method for Esterification using the Ph3P/CC14
`system., J. Org. Chem., 1985, 50, 4991
`M. Ramaiah, Cyclopentannulation Reactions in Organic Synthesis. Synthesis, 1984,
`7, 529
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`PATENTS:
`
`1.
`2.
`3.
`4.
`5.
`6.
`7.
`8.
`9.
`10.
`11
`
`Feb. 6, 1996
`US 548,9425
`Jan. 4, 1996
`WO96/00410
`Aug. 8, 1995
`US 543,9790
`Feb. 8, 1994
`US 5284,644
`Sep. 27, 1994
`US 535,0731
`Nov. 9, 1993
`US 526,0180
`Feb. 16, 1988
`US 472,5372
`Feb. 3, 1987
`US 4640,786
`Jul. 12, 1985
`EP 065,7301
`Apr. 23, 1985
`CA 1185,779
`US 61946538,(prov.) Feb 28, 2014
`
`0010
`10
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`Ramaiah Muthyala: Synthetic experience includes total and partial synthesis and modification of
`bioactive compounds (selected only) of the following structures:
`
`OH
`
`OH
`
`O
`
`NH
`
`COOH
`
`O
`
`O
`
`H
`
`O
`
`OH
`
`O
`
`OH
`
`O
`
`O H
`
`NH2
`
`H
`
`O
`
`OH
`
`OH
`
`O
`
`O
`
`OH
`
`OH
`
`O
`
`N
`
`COOH
`
`O
`
`OH
`
`OH
`H
`
`O
`
`O
`
`OH
`
`COOH
`
`O
`
`O
`
`O
`
`O
`
`H
`
`OH
`
`O
`
`N
`
`OH
`
`O
`
`H
`COOH
`
`H
`
`O
`H
`
`H
`
`NH
`
`H
`
`H
`
`O
`
`O
`
`N
`
`NH
`
`O
`
`OH
`
`NH O
`
`O
`
`NO
`
`OH
`
`OH
`
`H
`
`O
`
`O
`H
`
`O
`
`H
`
`H
`
`NH
`
`OH
`O
`
`NH2
`
`NH2
`
`O
`
`OH
`
`NH
`
`O
`
`OH
`O
`
`NH2
`
`N
`
`N
`
`N
`
`N
`
`O
`
`OH
`
`OH
`
`OH
`
`HOOC
`
`O
`OH
`
`O
`
`OH
`
`OH
`
`O
`
`OH
`
`OH
`
`COOH
`
`0011
`11