Engagingstudentsininterdisciplinaryresearchinchemistrylaboratorycoursetodiscovernewantibiotics

CHEM0745CUREOrganicChemistryLaboratoryCourse_AntibioticsDiscovery

Instructor:LingfengLiuemail:lfliu@pitt.eduSections:MoWe8-11:50am/MoWe1-4:50pm/TuTh8-11:50am/TuTh1-4:50pm

UniversityofPittsburghKennethP.DietrichSchoolofArtsandSciencesDepartmentofChemistry

v Yourjourney:Authenticrealworldresearchexperiencev Yourproject:Interdisciplinaryscienceadventuretodiscovernewantibioticsv Yourcontribution:SeekingforsolutionstotheAntibioticCrisisthatmankindis

facingv Yourtools:Advancedchemistry&microbiologytechniques

CourseDescription

SmallWorldInitiative(1credit)

CUREOrganicChemistryLab(2credits)

ControlStrain:LysobactorAntibioticus

UnknownStrain

DepartmentofBiologicalSciences

DepartmentofChemistry

Strainsdiscovery

AntibioticsDiscovery

AntibioticsDiscovery

Overview

•  Researchproject•  CurriculumDesign•  LabImplementation•  StudentResults•  Assessment

AntibioticCrisis

•  TacklingantibioticresistanceisahighpriorityforWHO.Aglobalactionplanonantimicrobialresistance,includingantibioticresistance,wasendorsedattheWorldHealthAssemblyinMay2015.

•  EachyearintheUnitedStates,atleast2millionpeoplebecomeinfectedwithbacteriathatareresistanttoantibioticsandatleast23,000peopledieeachyearasadirectresultoftheseinfections.

www.who.int www.cdc.gov

Deathsattributabletoantibioticresistance(orAMR),comparedwithothermajorcausesofdeath

https://amr-review.org/

StrategiesforAntibioticsDiscovery:PurificationoftheAntibiotics

I.AntibioticsProduction

II.AntibioticsExtraction

III.AntibioticsSeparation:ColumnChromatography

IV.AntibioticsPurification:HPLC

StrategiesforAntibioticsDiscovery:CharacterizationoftheAntibiotics

Nuclearmagneticresonance(NMR)spectroscopy

Infrared(IR)spectroscopy

MassSpectroscopy(MS)

Student-ledlabdynamicsmimickingresearchlabs

StudentResults:AntibioticsStructures

StudentResults:StructuralAnalysisof1,6-dimethoxyphenazine

StudentResults:StructuralAnalysisofActionomycinD

CUREOrganicChemistryLaboratoryCourseEnrollmentStatistics

Term Course # Credits Seats Offered Enrolled Fall 2015

(2161) CHEM 0330 1 2 × 8 16

Spring 2016 (2164) CHEM 0750 1 2 × 8 16

Fall 2016 (2171) CHEM 0750 2 2 × 12 24

Spring 2017 (2174) CHEM 0750 2 3 × 12 30

Fall 2017 (2181) CHEM 0745 2 3 × 12 32

Spring 2017 (2184) CHEM 0745 2 4 × 12 48

!

AssessmentoftheCURElab:CourseSurveyinFall2016

0

1

2

3

4

5

Collaboration Discovery Iteration

Chem0745

Chem0345

Likert-scalevalue

s

Total Surveys Scanned Valid Surveys CURE_Antibiotics (0750) 24 24

Standard (0345) 301 254

AssessmentoftheCURElab:CourseSurveyinSpring2017

0

1

2

3

4

5

CURElab

Standardlab

Total Surveys Scanned Valid Surveys CURE_Antibiotics (0750) 30 30

Standard (0345+0340) 507 396

Likert-scalevalue

s/Num

bero

fque

stions

Notes (0745vs…comparisonsin0320) 300 -18 -10 --- 272

32

Chem 0320 roster (excludes one G-grade student) Ws Got a letter grade but did NOT take the final

Relevant population

Chem 0745 roster (No Ws)

20 Concurrently enrolled in Chem 0320 in term 2181 (NO 0320 Ws) 20/32 = 62.5% of 0745 students concurrently in lecture.

286 -6

Chem 0345 roster Ws (4 of these 6Ws also withdrew from 0320; 3 of the 18 0320 Ws completed 0345)

154/286 = 53.8% of 0345 students concurrently in lecture.

(20+154)/(32+286) = 54.7% of Orgo 2 lab students were concurrently enrolled in lecture.

6

JoeGrabowski

5

Notes (0745 vs … comparisons in 0320)

6

300 students started Chem 0320; 282 were assigned a letter grade. 318 students started Orgo 2 Lab; 312 were assigned a letter grade. 318/300 == 6% larger lab enrollment than lecture enrollment.

(20+154)/300 = 58.0% of lecture students concurrently enrolled in lab. 154/300 = 51.3% of lecture students concurrently enrolled in 0345 lab. 20/300 = 6.7% of lecture students concurrently enrolled in 0745 lab.

438 unique individuals in 0320 and/or 0345 and/or 0745. Course Point Averages

(based on 500 course points): n=4 0745 Lab 391 78.1% n=71 0345 Lab 371 74.1% n=46 No Lab 358 71.6%

n=16 0745 Lab 399 79.8%

n=76 0345 Lab 344 68.8% n=69 No Lab 326 65.3%

JoeGrabowski

7

The 7 Spectroscopy ?s on the Final ACS Form 2016 Q15 Pick unknown given “no IR picks > 3080 cm-1; molecular ion @ 134. (Gen Chem 1;

Orgo 1; Orgo Lab)

Q23 If δ = 4.50ppm at 300 MHz, what is δ at 500 MHz. (Orgo 1; Orgo Lab)

Q31 Hydrolysis of 2-chloro-2-methylbutane, gives single product with shown 13C-NMR spectrum and a strong IR signal at 3375 cm-1; pick product. (Orgo 1; Orgo Lab)

Q42 Given 13C-NMR, pick the compound. (Orgo 1; Orgo Lab)

Q68 Match IR spectrum to one of four compounds. (Orgo 1; Orgo Lab)

Q69 Give SM for cross-coupling & 1H-NMR of product, pick product. (Orgo 1; Orgo Lab; Orgo 2)

Q70 Given 1H-NMR and some solubility information, pick the compound. (Orgo 1; Orgo Lab)

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JoeGrabowski

Gender, Orgo 2, Fall 2017 (2181)

Also concurrently enrolled in 0320

This table summarizes gender of all students in Organic Chemistry 2 (Chem 0320) in fall 2017 (Term 2181) (4th set of data in the table) AND the gender make-up of the lecture students in the Orgo 2 lab that they were concurrently enrolled in. The gender makeup of ALL students taking the two different versions of Orgo 2 lab is NOT included in the above table. (Total enrollment in Fall 2017 for Chem 0745 was 32 and for Chem 0345 was 286.)

The gender distribution in lecture mirrors the gender distribution in any of the three different lab conditions.

Male Female Total

0345 57 90 147 38.8% 61.2% 100.0%

0745 8 12 20 40.0% 60.0% 100.0%

No Lab 45 70 115 39.1% 60.9% 100.0%

0320 110 172 282 39.0% 61.0% 100.0%

JoeGrabowski

2 Sections Combined

Course Points (%)

Final Spec Score

Lab 0.109 0.146

No Lab -0.159 -0.219

# obs 282 272

% Lab 59.2% 59.9%

p 0.027 0.003

Effect Size 0.268 0.365

2 Sections Combined

Course Points (%)

Final Spec Score

0345 0.092 0.117

No Lab -0.118 -0.154

# obs 262 252

% 0345 56.1% 56.7%

p 0.091 0.032

Effect Size 0.210 0.272

2 Sections Combined

Course Points (%)

Final Spec Score

0745 0.553 0.956

No Lab -0.096 -0.175

# obs 135 129

% 0745 14.8% 15.5%

p 0.007 0.000001

Effect Size 0.649 1.131

2 Sections Combined

Course Points (%)

Final Spec Score

0745 0.445 0.690

0345 -0.061 -0.097

# obs 167 163

% 0745 12.0% 12.3%

p 0.033 0.001

Effect Size 0.506 0.787

Lab/NoLab,Orgo2,Fall2017(2181)•  “Course points” and “Final Spec Scores” are in Z-scores. •  All analyses on this slide combined the two sections of

Chem into a single cohort. •  “Final Spec Scores” is based on 7 questions on the 70-

questions, multiple choice final (ACS, Organic Form 2016). •  Effect size is always “better minus worse”: Lab – No Lab;

0345 – No Lab; 0745 – No Lab and 0745 – 0345. •  P values of less than 0.05 are significant and below 0.01,

highly so.

•  By either Course Performance in the entire 0320 lecture course, or by the 7 spectroscopy questions on the final exam for the lecture course, taking a lab is correlated with higher performance/scores.

• The biggest effect size is comparing “Final Spec Scores” between the 0745 Lab and the No Lab students.

• The second largest effect size (of the 8 presented) is comparing “Final Spec Scores” between the 0745 Lab and the 0345 Lab students.

• 7 of the 8 p values signify significance; only the Course Performance comparison of 0345 Lab and No Lab students has a p > 0.05.

JoeGrabowski

AcknowledgementsDepartmentofBiologicalSciencesJeanSchmidtEliaCrisucciNancyKaufmannJessicaRobertson

DepartmentofChemistryJoeGrabowskiKayBrummondGeorgeBandikErickaHuston

Fundingsupport:DepartmentofChemistry