KMap
Professor Robin Polt began doing chemistry at Indiana University - Purdue University at Indianapolis (IUPUI) on the Vietnam Era GI Bill with Prof. Martin O’Donnell.  At IUPUI he produced the first of the “O’Donnell Schiff bases” that are used to produce unusual and unnatural amino acids.  This methodology now appears in many undergraduate textbooks for Organic Chemistry and is widely used in industry.  While at IUPUI he was awarded a National Science Foundation Pre-Doctoral Fellowship.  Polt earned his Ph.D. at Columbia University in NYC with Prof. Gilbert J. Stork, one of the founders of Syntex Corp which introduced the first oral contraceptives in the late 1950s.  He completed his training in the art of Organic Synthesis with Prof. Dieter Seebach at the ETH in Zürich, Switzerland before coming to the University of Arizona in 1988.   Polt has continued to develop novel synthetic methods for amino acids, amino alcohols, glycosides and glycopeptides.  Application of these methods has resulted in the production of a number of pharmacologically active glycopeptides, alkaloid-like inhibitors of glycolipid processing enzymes and glycosyltransferases, as well as glycolipids with biological activity such as glycosphingolipids and rhamnolipids.  He discovered a new class of glycosphingolipids in the insect Manduca sexta— biologically active sphingomyelins and glycosides derived from dienylsphingosine, and he has developed methods for their synthesis, as well as the synthesis of rhamnolipids from Pseudomonas aeruginosa.  The biological focus of his work has been in attempting to understand the chemistry of carbohydrates (glycolipids & glycopeptides) at cell membranes, membrane trafficking, and using these insights to design glycopeptide drugs from endogenous peptide neurotransmitters (neuromodulators, hormones) with enhanced stability in vivo that are capable of penetrating the Blood-Brain Barrier.  In addition to lecturing and laboratory teaching he has mentored a large number of undergraduate, graduate (19 Ph.D.s   His Ph.D.s have hailed from the US (10), Czech Republic*, China, India, Iran*, Ireland, Kenya*, Korea, Mexico* and Sri Lanka.  Four of these Ph.D. students (*) have gone on to become naturalized citizens or permanent resident status.  Recent undergraduates associated with Polt’s research group have gone to graduate schools at Harvard, MIT, Boston University, University of Wisconsin, and Columbia University.  Polt’s research has been supported by the National Science Foundation (NSF), the National Institute of Neurological Disease and Stroke (NINDS), the US Army, the Office of Naval Research (ONR), the Michael J. Fox Foundation and the Migraine Research Foundation, in addition to industrial support, now totalling over $15M.  His current research work is supported by NINDS and is directed toward the development of neuroprotective drugs for Parkinson’s Disease from endogenous neuropeptides, as well as NSF-EPA studies done in collaboration with the Pemberton group on the development of "green" surfactants. We have recently begun collaboration with Joe Garcia's group at the Medical School on the development of Sphingosine-1-Phosphate receptor agonists for the treatment of lung injury.  We have submitted a new RO1 to NIH to support this work. Besides Jeanne Pemberton's GlycoSurf start-up, which was based on "Polt technology" licensed to them, a second start-up owned by Meredith Hay called ProNeurogen has licensed IP from us regarding glycosylated angiotensin analogues as neuroprotective compounds, and one of these compounds is now entering clinical trials for the treatment of post-surgical dementia.  Note that I have no equity position in either of these companies, but I do retain 17% ownership in our Deleware based company, Biousian Biosystems, Inc.  Further, we are starting a new company called Teleport Pharmaceuticals in order to exploit our chemistry to produce centrally active drugs based on peptide neurotransmitters.
Courses
  • CHR
    Chemical Hygiene and Regulations

  • BLS
    Basic Laboratory Safety

  • LOC
    Lectures in Organic Chemistry

  • SMO
    Synthetic and Mechanistic Organic Chemistry

  • OP
    Organic Preparations

  • ALS
    Advanced Laboratory Safety

  • IPT
    Introduction to Pharmacology and Toxicology Research

  • AOC
    Advanced Organic Chemistry

  • ASO
    Advanced Synthetic Organic Chemistry

  • IPD
    Introduction to Pharmacology, Drug Discovery & Pharmaceutics

Student Thesis/Dissertation
  • Development of Immune Modulators Targeting Autoimmune Disorders and Pulmonary Injury: Design, Synthesis, and Biological Evaluation of Sphingolipid-Derived Sphingosine-1 Phosphate Receptor 1 Agonists

    2022

    doctoral
  • Synthesis, Comprehensive Characterization, and Development of Therapeutic Peptides and Glycopeptides for Targeted Respiratory Drug Delivery as Inhalation Aerosols

    2021

    doctoral
  • Design, Synthesis, and Evaluation of Brain-Penetrant PACAP-Derived Glycopeptides for the Treatment of Neurodegeneration and Neuroinflammation

    2021

    doctoral
  • Synthesis and Characterization of Bio-inspired Glycolipid Surfactants

    2018

    doctoral
  • Creating a C-12 Series of Glycolipids for Use as Micelles in Drug Delivery

    2017

    bachelors
  • Design and Synthesis of Neurologically Active Glycopeptides for Neuroprotection and Antinociception

    2016

    doctoral
  • Design and Synthesis of PACAP Based Glycopeptide Analogs; Effects of Glycosylation on Activity and Blood-Brain Barrier Penetration

    2014

    doctoral
Grants
  • Funding agency logo
    Oxytocin Analgesics Without Side Effects for Opioid Use Disorder

    Principal Investigator (PI)

    2022

    $100.0K
    Active
  • Funding agency logo
    Development of a Selective Mu-Delta Opioid Receptor Heterodimer Antagonist for Enhancing Opioid Analgesia while Reducing Side Effects

    Co-Investigator (COI)

    2021

    $499.4K
    Active
  • Funding agency logo
    Glycosylated Endomorphin Analogs for Treatment of Opioid Use Disorder (OUD)

    Principal Investigator (PI)

    2021

    $46.0K
  • Funding agency logo
    MOR/DOR Heterodimer Antagonists: A Novel Treatment for Opioid Dependence

    Co-Investigator (COI)

    2019

    $1.2M
  • Funding agency logo
    PACAP/VIP Glycopeptide Agonists as Neuroprotective Therapies for Parkinson's Disease

    Principal Investigator (PI)

    2015

    $2.0M
  • Funding agency logo
    PACAP Antagonists as Novel Migraine Therapies

    Principal Investigator (PI)

    2014

    $25.0K
  • Funding agency logo
    NSMDS: Molecular Design, Synthesis and Characterization of Green Glycolipid Surfactants

    Co-Investigator (COI)

    2013

    $4.5M
  • Funding agency logo
    Opioid glycopeptides for the treatment of levodopa-induced dyskinesia

    Co-Investigator (COI)

    2012

    $75.0K
Technologies / Patents
      News
      • Following nature's rules, researchers develop new methods for treating degenerative neurological disease

        2022

      • UA Startup Advances New Therapies for Vascular Dementia

        2017

      • UA Research goes from Idea to Patent to Market

        2015

      • Catapulting UA Discoveries to the World

        2014

      • UA Pain Research Team Awarded $2.5M to Tackle Chronic Pain

        2013

      • UA Student Earns Howard Hughes Award

        2009

      • Interdisciplinary UA, NAU Team Receives $3.3 million to Study Biosurfactants

        2007

      • Valley Fever Drug Phase 1 and 2 Clinical Trial Funded

        2007

      • UArizona reports record number of inventions

      Publications (115)
      Recent
      • Design and Synthesis of Novel Brain Penetrant Glycopeptide Analogues of PACAP with Neuroprotective Potential for Traumatic Brain Injury and Parkinsonism.

        2022

      • Spray-Dried Inhalable Powder Formulations of Therapeutic Proteins and Peptides.

        2021

      • Synthesis, Physicochemical Characterization, In Vitro 2D/3D Human Cell Culture, and In Vitro Aerosol Dispersion Performance of Advanced Spray Dried and Co-Spray Dried Angiotensin 1-7) Peptide and PNA5 with Trehalose as Microparticles/Nanoparticles for Targeted Respiratory Delivery as Dry Powder Inhalers.

        2021

      • Lessons in Stereochemistry: Resolution, Synthesis, and Characterization of Chiral Compounds

        2020

      • The Delta-Specific Opioid Glycopeptide BBI-11008: CNS Penetration and Behavioral Analysis in a Preclinical Model of Levodopa-Induced Dyskinesia

        2020

      • Glycopeptide drugs: A pharmacological dimension between Small Molecules and Biologics

        2020

      • Characterization of Delta Opioid Receptor Activity of MMP2200, a Mixed Efficacy Mu and Delta Opioid Receptor Agonist

        2020

      • Organic Solution Advanced Spray-Dried Microparticulate/Nanoparticulate Dry Powders of Lactomorphin for Respiratory Delivery: Physicochemical Characterization, In Vitro Aerosol Dispersion, and Cellular Studies.

        2020

      • Sphingosine-1-phosphate receptor-independent lung endothelial cell barrier disruption induced by FTY720 regioisomers.

        2020

      • In silico Docking Studies of Fingolimod and S1P1 Agonists.

        2020

      • Biodegradability and toxicity of cellobiosides and melibiosides

        2020

      • Behavioral pharmacology of the mixed-action delta-selective opioid receptor agonist BBI-11008: studies on acute, inflammatory and neuropathic pain, respiration, and drug self-administration

        2020

      • Highly-selective µ-opioid receptor antagonism does not block L-DOPA-induced dyskinesia in a rodent model.

        2020

      • Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers

        2019

      • The combination of the opioid glycopeptide MMP-2200 and a NMDA receptor antagonist reduced L-DOPA-induced dyskinesia and MMP-2200 by itself reduced dopamine receptor 2-like agonist-induced dyskinesia

        2018

      • An update on sphingosine-1-phosphate receptor 1 modulators.

        2018

      • The opioid glycopeptide MMP-2200: Analysis in preclinical models of L-DOPA-induced dyskinesia

        2017

      • Synthesis and Characterization of Four Diastereomers of Monorhamnolipids

        2017

      • Alkyl-melibioside and Alkyl-cellobioside Solution Phase Properties: Effect of Sugar Headgrouand Alkyl Chain Length on Surfactant Performance

        2016

      • Preparation of S-Glycoside Surfactants and Cysteine Thioglycosides

        2016

      • The mixed-action delta/mu opioid agonist MMP-2200 does not produce conditioned place preference but does maintain drug self-administration in rats, and induces in vitro markers of tolerance and dependence

        2015

      • CNS active O-linked glycopeptides.

        2015

      • Glycolipids and glycopeptides: Minimally competent Lewis acid catalysis produces surfactants for use ex vivo and in vivo

        2015

      • Structural Requirements for CNS Active Opioid Glycopeptides

        2015

      • A PM-IRRAS Investigation of Monorhamnolipid Orientation at the Air-Water Interface

        2013

      • CNS penetration of the opioid glycopeptide MMP-2200: a microdialysis study.

        2012

      • Opioid glycopeptide analgesics derived from endogenous enkephalins and endorphins

        2012

      • Minimally Competent Lewis Acid Catalysts: Indium(III) and Bismuth(III) Salts Produce Rhamnosides 6‐Deoxymannosides) in High Yield and Purity

        2012

      • Glycosylation of α-amino acids by sugar acetate donors with InBr3. Minimally competent Lewis acids

        2012

      • Effects of the novel glycopeptide opioid agonist MMP-2200 in preclinical models of Parkinson's disease

        2011

      • Phosphorylation of enkephalins: NMR and CD studies in aqueous and membrane-mimicking environments

        2011

      • (S)Methyl 2-S)2-bis(4-methoxyphenyl)methylideneamino]3- hydroxypropanamido}3-methylbutanoate

        2011

      • In vivo characterization of MMP-2200, a mixed δ/μ opioid agonist, in mice

        2011

      • (S)Methyl 2-S)2-bis-4-meth-oxy-phen-yl)methyl-idene-amino]3-hy-droxy-propanamido}3-methyl-butano-ate.

        2010

      • Serine and threonine Schiff base esters react with β-anomeric peracetates in the presence of BF sub 3 sub ·Et sub 2 sub O to produce β-glycosides

        2010

      • Synthetic Method for the Development of Monorhamnolipids

        2010

      • Glycosyl-enkephalins: synthesis and binding at the mu, delta kappa opioid receptors. Antinociception in mice

        2009

      • Assessment of the efficacy and side effect profile of morphine and MMP2200, a mixed delta/mu agonist

        2009

      • Structural studies on the neutral glycosphingolipids of Manduca sexta.

        2008

      • Endoglycosidases: Biochemistry, Biotechnology, Application Edited by Masahiko Endo Hirosaki University, Aomori, Japan) Sumihiro Hase Osaka University, Osaka, Japan) Kenji Yamamoto Kyoto University, Kyoto, Japan) and Keiichi Takagaki Hirosaki University School of Medicine, Aomori, Japan) Kodansha Ltd: Tokyo and Springer: Berlin, Heidelberg, New York. 2006. xvi 255 pp. 169.00. ISBN 4-06-212192-2 Kodansha) and 3-540-34494-2 Springer)

        2008

      • Behavioral pharmacology of the μ/δ opioid glycopeptide MMP2200 in rhesus monkeys

        2008

      • Glycosylation improves the central effects of DAMGO

        2007

      • Sugar synthesis from a gas-phase formose reaction

        2007

      • Enkephalin glycopeptide analogues produce analgesia with reduced dependence liability

        2006

      • Glycosylated neuropeptides: A new vista for neuropsychopharmacology?

        2005

      • N-DIPHENYLMETHYLENE-PROTECTED GLYCOSYL ACCEPTORS SELECTIVE BETA-O-GLYCOSYLATION TO FORM LACTOSYL-THREO-CERAMIDES

        2005

      • Improved bioavailability to the brain of glycosylated Met-enkephalin analogs

        2005

      • Biousian glycopeptides penetrate the blood-brain barrier

        2005

      • INVESTIGATING THE INTERSTELLAR CHEMISTRY LEADING TO SIMPLE SUGARS

        2005

      • New prospects for glycopeptide based analgesia: Glycoside-induced penetration of the Blood-Brain Barrier

        2005

      • New PDMP analogues inhibit process outgrowth in an insect cell line

        2004

      • Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta

        2004

      • Antinociceptive structure-activity studies with enkephalin-based opioid glycopeptides.

        2004

      • BETA-AMINO ALCOHOLS FROM AMINO-ACIDS CHELATION CONTROL VIA SCHIFF-BASES

        2004

      • Optically active 4- and 5-coordinate transition metal complexes of bifurcated dipeptide Schiff bases

        2003

      • Glycopeptide-membrane interactions: Glycosyl enkephalin analogues adopt turn conformations by NMR and CD in amphipathic media

        2003

      • GLYCOPEPTIDE ENKEPHALIN ANALOGS PRODUCE ANALGESIA IN MICE EVIDENCE FOR PENETRATION OF THE BLOOD-BRAIN-BARRIER

        2003

      • Deprotonation of Chelating Enamines. Direct Formation of β‐Lithio Enamines.

        2002

      • Glycopeptide analgesics

        2001

      • Lipo α-amino-β-hydroxy acids and O-linked glycosides: Building blocks for ceramyl and glycosphingoyl peptides

        2001

      • Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin.

        2001

      • O-linked glycopeptides retain helicity in water

        2001

      • Enkephalin glycopeptide analogues produce analgesia with reduced dependence liability.

        2000

      • AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C C-O BOND FORMATION

        2000

      • Lipid Synthesis and Manufacture Edited by Frank D. Gunstone Professor Emeritus, University of St. Andrews, Dundee, Scotland) CRC Press: Boca Raton. 1999. xv 472 pp. 135.00. ISBN 0-8493-9737-5.

        2000

      • Antinociceptive structure-activity studies with enkephalin-based opioid glycopeptides

        2000

      • Enkephalin-based drug design: conformational analysis of O-linked glycopeptides by NMR and molecular modeling

        2000

      • Asymmetric syntheses of 8-epi-swainsonine triacetate and 1,2-di-epi-swainsonine. Carbonyl addition thwarted by an unprecedented aza-pinacol rearrangement

        2000

      • ALKYLATION OF IMIDAZOLIDINONE DIPEPTIDE DERIVATIVES PREPARATION OF ENANTIOMERICALLY PURE DIPEPTIDES AND TRIPEPTIDES BY CHIRALITY TRANSFER VIA A PIVALALDEHYDE N,N-ACETAL CENTER

        2000

      • Improved bioavailability to the brain of glycosylated Met-enkephalin analogs.

        2000

      • Glycosidase inhibitors: Synthesis of enantiomerically pure aza-sugars from Schiff base amino esters via tandem reduction-alkenylation and osmylation

        1999

      • Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases

        1998

      • Glycosyltransferase inhibitors: Synthesis of D-threo-PDMP, L-threo- PDMP, and other brain glucosylceramide synthase inhibitors from D- or L- serine

        1998

      • SYNTHESES OF IMINOLYXITOLS VIA TANDEM REDUCTION-ALKENYLATION OF O DONNELL S SCHIFF BASES

        1998

      • STEREOSELECTIVE SYNTHESIS OF O-SERINYL/THREONINYL-2-ACETAMIDO-2-DEOXY-ALPHA-GLYCOSIDES OR O-SERINYL/THREONINYL-2-ACETAMIDO-2-DEOXY-BETA-GLYCOSIDES

        1997

      • General method for the synthesis of N-methyl amino acids and N-alkyl amino esters from O'Donnell's Schiff bases

        1997

      • Amino acid-derived ligands for transition metals: Catalysis via a minimalist interpretation of a metalloprotein

        1997

      • New chemical method for synthesis of O-linked glycopeptides

        1996

      • DESIGN AND SYNTHESIS OF PEPTIDE LIGANDS WITH UNIQUE BIOCHEMICAL AND BIOLOGICAL PROFILES AT OPIOID RECEPTORS THAT CROSS THE BLOOD BRAIN BARRIER

        1995

      • Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

        1995

      • Piperidine Triols via Enantioselective Alkylation and Osmylation of Alanine Schiff Base Esters

        1995

      • Preparation of monosilyl acetals from esters via iBu sub 2 sub AlH reduction and trapping with N-trimethylsilyl)imidazole. Addition of allyltrimethylsilane to yield homoallylic alcohols or ethers

        1995

      • An enantioselective synthesis of N-methylfucosamine via tandem C-C/C-O bond formation

        1994

      • New opioid compounds in analgesia

        1994

      • ASSESSMENT OF AN IN-VITRO BLOOD-BRAIN-BARRIER MODEL USING SEVERAL MET5]ENKEPHALIN OPIOID ANALOGS

        1994

      • A systematic study of glycolaldehyde in sagittarius B2(N) at 2 and 3 mm: Criteria for detecting large interstellar molecules

        1994

      • Glycopeptide enkephalin analogues produce analgesia in mice: evidence for penetration of the blood-brain barrier.

        1994

      • Stereoselective synthesis of β-D-glycopyranosyl-L-serinate or threoninate derivatives with an unusual migration

        1994

      • N-diphenylmethylene-protected glycosyl acceptors. Selective β-O-glycosylation to form lactosyl-threo-ceramides

        1993

      • Determination and metabolism of dithiol chelating agents. XV. The meso- 2,3-dimercaptosuccinic acid-cysteine 1:2) mixed disulfide, a major urinary metabolite of DMSA in the human, increases the urinary excretion of lead in the rat

        1993

      • GENERAL-METHODS FOR ALPHA-O-SER/THR OR BETA-O-SER/THR GLYCOSIDES AND GLYCOPEPTIDES SOLID-PHASE SYNTHESIS OF O-GLYCOSYL CYCLIC ENKEPHALIN ANALOGS

        1993

      • O-GLYCOPEPTIDES A SIMPLE BETA-STEREOSELECTIVE GLYCOSIDATION OF SERINE AND THREONINE VIA A FAVORABLE HYDROGEN-BONDING PATTERN

        1993

      • Assessment of an in vitro blood-brain barrier model using several Met5]enkephalin opioid analogs.

        1993

      • β-Alkoxy Schiff base–oxazolidine tautomerism: solid-state structure of N-diphenylmethylene-l-threonine methyl ester

        1993

      • Catalysis by amino acid-derived tetracoordinate complexes: Enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes

        1992

      • A synthetic method for unsymmetrical disulfides of cysteine: the bis-cysteine disulfide of meso-2,3-dimercaptosuccinic acid.

        1992

      • General Methods for α- or β-O-Ser/Thr Glycosides and Glycopeptides. Solid-Phase Synthesis of O-Glycosyl Cyclic Enkephalin Analogues

        1992

      • Aluminoxy acetals from α-amino esters: Chirality transfer via sequential addition of hydride and C-nucleophiles. 2-Amino alcohols and sphingosines

        1992

      • E-1-lithio-1-alkenes in hydrocarbon solvent

        1992

      • Improved blood-brain barrier penetration and enhanced analgesia of an opioid peptide by glycosylation

        1991

      • Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

        1991

      • O-glycopeptides: a simple β-stereoselective glycosidation of serine and threonine via a favorable hydrogen bonding pattern.

        1991

      • β-Amino alcohols from amino acids: Chelation control via schiff bases.

        1990

      • Stereoselective alkylation of glycine units in dipeptide derivatives: Chirality transfer via a pivalaldehyde N,N-acetal center

        1989

      • Acidities of glycine Schiff bases and alkylation of their conjugate bases

        1988

      • Theoretical studies of the lithiation of enamines

        1988

      • STEREOSELECTIVE ALKYLATION OF GLYCINE UNITS IN DIPEPTIDE DERIVATIVES CHIRALITY TRANSFER VIA A PIVALALDEHYDE N,N-ACETAL CENTER

        1987

      • Alkylation of Imidazolidinone Dipeptide Derivatives: Preparation of Enantiomerically Pure Di‐ and Tripeptides by ‘Chirality Transfer’ via a Pivalaldehyde N,N‐Acetal Center. Preliminary Communication

        1987

      • Deprotonation of chelating enamines. Direct formation of β-lithio enamines

        1986

      • Preparation of an Electrophilic Glycine Cation Equivalent and Its Reaction with Heteroatom Nucleophiles. The Synthesis of Amino Acids by Reaction of an Electrophilic Glycine Cation Equivalent with Carbon Nucleophiles.

        1985

      • Preparation of an electrophilic glycine cation equivalent and its reaction with heteroatom nucleophiles

        1985

      • X-ray crystal structure of N-2-lithiocyclohexenyl)N,N′,N′-trimethyl-1,3-propanediamine: A pentavalent lithium?

        1984

      • A mild and efficient route to Schiff base derivatives of amino acids

        1982

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