Research, Teaching, and Professional Development at a

Research: Science and Education

Research, Teaching, and Professional Development at a Comprehensive University David B. Ball,* Mike Wood, Craig Lindsley, Paul Mollard, D. J. Buzard, Randy Vivian, Max Mahoney, and Benjamin R. Taft Department of Chemistry, California State University, Chico, Chico, CA 95929-0210; *[email protected]

The relationship between research and teaching and the benefits these endeavors bring to the student, the faculty member, and the institution along with the pitfalls that accompany it have been amply discussed in this Journal over the past seventy-plus years (1). At many undergraduate institutions, chemistry students’ educational experience once mainly consisted of lecture and accompanying laboratory, where “cookbook” chemistry was the norm. Relatively few students had the opportunity to participate in any significant undergraduate research. Today, many faculty in most chemistry departments are partially to fully engaged in undergraduate research (2). In fact, it has been pointed out that it has taken much time and effort on the part of those who advocate undergraduate research to have it considered in the same regard as research carried out at Ph.D. granting institutions (3). Expectation To Publish Administrators at most undergraduate institutions now expect new and tenured faculty to be professionally active as judged by publications and the gaining of contracts and grants. With relatively heavy teaching loads of 9–12 units per semester or quarter and committee work, chemistry faculty have a difficult time finding the hours required to carry out quality research that meet their administrations’ expectations for tenure and promotion. Undergraduate researchers can play a vital role in the endeavor to be successful in these efforts, benefiting both the faculty and student alike. However, faculty need to exercise caution in how they utilize undergraduates in their research and they must not lose sight of the mission to teach. Our students must be an integral part of the learning process and not just a “pair of hands” manipulating molecules for the benefit of the faculty. They need to be collaborators who fully participate in the learning and research process leading to increased student– faculty scholarship. Participation in undergraduate research provides the student researcher avenues for intellectual and scientific growth on the path to becoming a scientist. These paths traverse a course from formal study in the classroom or laboratory to the relatively independent atmosphere of chemical research in graduate school or industry. Definition of Undergraduate Research What then is undergraduate research? It has been defined by the Council on Undergraduate Research (CUR) as “an inquiry or investigation conducted by an undergraduate that makes an original intellectual or creative contribution to the discipline” (4). We believe that this definition unduly sets limits that would seem to exclude as research student laboratory activities that comprise the training process by 1796

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which students learn to become independent researchers. Also, many comprehensive universities do not have the financial resources to support student–faculty research, in terms of time and money, at the level necessary for undergraduate researchers to make truly original contributions to the discipline (5). Over the past decade or so, as undergraduate institutions have “raised the bar” for gaining tenure and promotion, new tenure-track faculty have been duly allocated, where possible, extra units of release time and modest start-up funds with the expectation of increased scholarly productivity. However, scholarly activity, as judged by publication data, appears to actually have decreased over this same time period (6). Even more unexpectedly, another earlier study documented that fewer than 50% of publications from the 11 most prolific undergraduate institutions had student coauthors (7). It is our belief that defining undergraduate research as stated by CUR does not provide for an accurate evaluation of the extent nor quality of student–teacher research activities at many comprehensive universities. It is not our contention that the ultimate goal of undergraduate research should not be peer-reviewed publications but that, often, faculty–student research efforts are evaluated solely as teaching. The retention, tenure, and promotion (RTP) criteria at Chico State have evolved to just this point. In the RTP process a faculty member will receive credit for student coworkers involved in research in the “teaching category”. Until these efforts result in a scholarly work, credit is not given in the “professional development category”. This type of evaluation of undergraduate research will normally result in negative decisions towards tenure and promotion by administrators. In addition, it has become obvious at Chico State that the nontenured faculty, concerned about their professional development as judged by scholarly works, have concentrated their efforts in this area while neglecting developing the teaching skills required to be successful in the classroom. New Definition Needed The current hiring process exacerbates this problem in that potential hires are more thoroughly evaluated on their research potential and their ability to garner extramural funding than they are on their potential to become outstanding teachers of chemistry. It definitely is more difficult to fairly evaluate as professional development research activities that do not result in publications. Yet, it is believed that throughout the chemical education community there are a large number of chemistry faculty involved in the type of activity that does not result in timely scholarly works. Appropriate evaluation guidelines should be established by the American Chemical Society to cover a broader definition of undergraduate research activities. This should result in an added institu-

Vol. 81 No. 12 December 2004

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tional emphasis on teaching that in turn would improve the quality of classroom instruction and even expand the undergraduate research experience at comprehensive institutions. Over the past 20 years, approximately 35 Chico State undergraduates have gone on to earn a Ph.D. in chemistry while during this same period, there have been only 5 student coauthored articles published. We have been relatively proficient in providing our students the necessary training in the classroom and the research laboratory such that they are successful in graduate school.1 The remaining part of this article will briefly outline an ongoing undergraduate research project in which 14 students have participated over the past 16 years. Many of these students succeeded in their chemistry careers after their undergraduate research experience. Of these students, two are currently undergraduates while nine of the others have since received Ph.D.s in organic chemistry. This is the first peer-reviewed account of their undergraduate research efforts.2

Borrelidin is a macrolide antibiotic that was first isolated from Streptomyces rochei in 1949 (9). It possesses high in vivo activity against Borrelia species by inhibiting the action of threonyl-tRNA synthetase (10). Its macrolide structure with nine chiral centers presents a challenge to the synthetic organic chemist.3 In a convergent synthetic approach, borrelidin may be thought of being comprised of three portions: top, southwest, and southeast portions (Figure 2). Synthetically dissecting these portions, one arrives at specific synthetic targets. Model studies for the connection of the three portions to form a molecule ready for macrolide lactonization has been studied by three students at Chico State and is based on an aldollike condensation of the aldehyde of a completed top portion with a commercially available southeast portion alkylated with the previously assembled southwest portion (11). Two students have worked on the top portion while the majority of the students involved in this project have worked on the racemic and chiral syntheses of the southeast portion 2.

The Research Project

Results and Discussion

In the academic year 1982–1983, I (DBB) spent a year sabbatical at the University of California, Santa Cruz working in the laboratories of David Morgans. This year changed the way I thought about chemistry and more importantly changed the way I did chemistry. Even though I was trained as a physical organic chemist, I had been involved in several synthetic projects in my Ph.D. and postdoctoral work. But I did not know how modern techniques in synthetic organic chemistry have given the chemist a whole new arsenal for making synthetically challenging molecules. Morgans, fresh from a Ph.D. with Gilbert Stork at Columbia University, gave me the opportunity to learn syringe techniques, manipulations of reagents at subambient temperatures and under inert atmosphere, flash chromatography, medium-pressure liquid chromatography (MPLC), and high-field NMR spectroscopy. The project that provided me these laboratory skills was the synthesis of borrelidin 1 (Figure 1). It was with these skills and renewed professional vitality that I returned to Chico State to embark on the training of our students in modern synthetic organic chemistry.

The first students engaged on the borrelidin project were confronted not only with the challenges that they faced in the laboratory but also by the instrumentation available to analyze the results of their research efforts. On a daily basis until 2000, our students relied on a 1984 continuous-wave Varian EM360 for structural identification of their products by proton NMR and did not have 13C spectra to aid in their structure elucidation. However, at times, we were able to call on our colleagues at UC, Santa Barbara and UC, Santa Cruz for needed spectral data of several key intermediates. Most of the students who have worked on this project did so dur-

H

H O

top portion

O O OR

top portion

southwest portion

HO

S

OH O

X

NC H

southwest portion

CO2H

southeast portion

1

H HO2C

2 Figure 2. Portions of borrelidin used as synthetic targets.

Figure 1. Structure of borrelidin.

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OP

O

H

southeast portion

NC

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ing the academic year, spending relatively few hours a week in the laboratory. This fact, coupled with the excessive turnaround time needed for obtaining off-campus NMR spectra, meant that individual accomplishments were never dramatic. In fact, several undergraduate coworkers, though learning laboratory techniques by repeating prior students’ work, did not significantly contribute to moving the project forward. Yet each of these students came away from their “research experience” motivated to pursue a career in chemistry either in graduate school or industry. Four events occurred at Chico State that have recently increased our students’ productivity in the laboratory and in undergraduate research.4 We have offered an advanced organic laboratory course, instituted a year-long honor research requirement, received $40,000 from Roche Bioscience for student stipends to do research in organic synthesis, and obtained an NSF CCLI grant allowing us to purchase a high field FT–NMR spectrometer.5 These events have greatly contributed to the near completion of the southeast portion of borrelidin. The reaction sequence leading to the synthesis of epoxide 3, an immediate precursor to 2 (the southeast portion of

borrelidin), is shown in Scheme I. Working on this project has provided our undergraduate researchers with the tools to be successful in becoming synthetic organic chemists. The required laboratory skills and techniques to master are extensive. These include classic protection and deprotection reactions, following reaction progress by thin-layer chromatography (TLC), syringe and cannula techniques, use of alkyllithium at subambient temperatures under an inert atmosphere, stereoselective partial hydrogenation of an alkyne,6 racemic and enantioselective epoxidation of a cis alkene, intramolecular cyclization (Baldwin’s rules7), various purification techniques including flash chromatography and MPLC and Kugelrohr distillation,8 enantiomeric excess determination by both NMR and chiral GC analysis, and spectral analysis of reaction products utilizing NMR spectrometry (1H and 13C; 1D and 2D experiments) and GC–MS.9 Over the years, three different students have worked on the asymmetric synthesis of 3. Two of the students investigated the Sharpless asymmetric epoxidation (13) while the third looked at the Jacobsen asymmetric epoxidation (14) (Scheme II). The application of Sharpless or Jacobson methodology has not been overly successful. The proposed con-

Br

H

H HCl 98%

HO

Cl

n-BuLi

DHP

THF −78 °C

THPO

HMPA −78 °C to 0 °C 88%

KCN

CN

Cl

THPO

THPO

DMF 100 °C 82%

H2, Pd/CaCO3/Pb

H

H

THPO

CN

MeOH 88%

NC

NC

O

TsO

H NaOMe

TsCl

O

H

THF −78 °C 66–90%

H

H 41%

pyr 90%

LDA or NaN(TMS)2

THPO

PPTS

H

(racemic)

OH

HO

O

H

CN

CH2Cl2 83%

OH

HO

O

THPO

quinoline, MeOH 90%

NaOH, EtOH, H2O

H

MCPBA

O O

43%

H MeO2C

H

3 Scheme I. Reaction sequence leading to the synthesis of epoxide 3, an immediate precursor to 2 (the southeast portion of borrelidin).

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version of epoxide 3 to the methyl ester of the southeast portion of borrelidin is shown in Scheme III. The chemistry in this reaction sequence, though based on chemistry from 1981, has been developed only recently (15). The utilization of organometallic reagents (Schwartz’s reagent and higher-order cuprates) in organic synthesis takes the chemistry from the 1980s to 2003. Conclusions The convergent synthesis of borrelidin continues to be an actively pursued research project by undergraduate chemistry students at Chico State. The varied laboratory techniques, chemistry, and required spectral analyses give our

Sharpless Epoxidation THPO CN

MeOH

PPTS

HO CN

(+)-DET, Ti(Oi-Pr)4

CH2Cl2, −23 °C 4 Å sieves t-BuOOH 58%

CN HO H

H

O

2S, 3R 49% ee

students a rich undergraduate research experience. These experiences have “jump-started” their chemistry careers in graduate school and industry. Of the 14 students who have participated in this research project, two are currently undergraduates (CSU, Chico and Cal Poly, SLO). Of the graduates, one went directly to industry; one attended graduate school but did not receive a degree, has worked in the pharmaceutical industry, and is now a part-time chemistry instructor at Chico State; and one received a MS degree from UC, Irvine and works at Pfizer. Of the nine other students who received Ph.D.s in organic chemistry, one attended Cornell and the others attended UCSB. Five of these students have had postdoctoral positions at Harvard. Other postdoctoral positions were at Colorado State, and Imperial College, London, while another student declined a position at Stanford. Eight of these postdoctoral positions were supported by NIH postdoctoral fellowships. These former students’ current employment in the pharmaceutical industry include Merck, Bristol-Meyers-Squibb, Johnson & Johnson, and Neurocrine Biosciences. Each student who has worked on borrelidin has made a positive contribution to the project with most helping to move this project towards completion. Individual accomplishments have varied greatly such that a number of these student research activities might not be classified as “original or creative”. Yet both students and teacher have greatly benefited from each student’s involvement in this research project. However, using the RTP criteria of today, the student–faculty borrelidin research activities would simply be categorized as “teaching” and not as “professional development” as scholarly works were not forthcoming. With the current emphasis of the tenure and promotion process on scholarly productivity, a newly hired chemistry faculty member would be taking a chance to embark on a long-term research project with undergraduates with the expectation of a positive decision on tenure and promotion in the allocated tenure timeline. But if the chemical community decides that there is

TIPS Protection and Jacobsen Epoxidation

TBS-Cl imidazole DMF

HO

TIPSCl

4 steps

imidazole DMF 80%

45% overall

TBSO Cp2Zr(H)Cl

H HO

2 eq MeLi

THF

−78 °C

TIPSO CN

2-ThCu(CN)Li OTBS

NaOCl, CH2Cl2, 4 °C

OH

Jacobsen's catalyst

H

CN TIPSO H

O

methyl ester 2

H

Scheme II. Two reaction schemes used to synthesize the southeast portion of borrelidin.

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O

MeO 2 C

•

H MeO2C

3

Scheme III. The proposed conversion of epoxide 3 to the methyl ester of the southeast portion of borrelidin, 2.


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much to be gained by both faculty and students at comprehensive institutions from engaging in undergraduate research that does not immediately lead to scholarly works, projects such as borrelidin would be evaluated as professional development. Acknowledgments We would like to acknowledge the Department of Chemistry and the College of Natural Sciences at CSU, Chico for financial support, sabbatical leaves, and establishing the RTP process that fostered this long-term research project. Also, appreciation is extended to those seven undergraduate researchers who participated in the borrelidin project over the years but were not listed as coauthors. Finally, acknowledgment must be given to the referees who read this manuscript. It is by their thoughtful and valued input that the manuscript took its final form. Notes 1. An article by Bruce Lipshutz in Acc. Chem. Res. highlights the success of Chico State students in graduate school (8). 2. Students have presented their contributions to this project in presentations at Chico State and elsewhere. A poster on the southwest portion of borrelidin was presented at the 225th national meeting of the ACS (CHED 597), New Orleans, March 2003 and an oral presentation was given at the 15th Annual ACS Undergraduate Research Symposium at the University of San Francisco, May 3, 2003. 3. The synthetic sequence described here was proposed by David Morgans in 1981. To our knowledge there has been at least one group actively engaged in the total synthesis of borrelidin. The research group of James P. Morken of UNC, Chapel Hill has published an elegant reaction sequence for the total synthesis of borrelidin (16). It is interesting to note that the sequence described herein has no common steps with the Morken sequence. Whereas, the chemistry from 1981 includes resolving enantiomers (the top portion), the Morken process entails only enantioselective syntheses utilizing reactions from the post-1981 era. 4. This can be documented by the number of posters our students have presented at national ACS meetings recently and coauthorship on several publications (12). 5. A NSF Course, Curriculum and Laboratory Improvement Program Grant #99-50413 allowed us to purchase a Varian 300VX NMR spectrometer that has been in operation since February 2000. 6. Until a high-field FT–NMR and a GC–MS were available to our students, it was not known that the hydrogenation gives approximately 10% of the trans alkene. 7. For a discussion of Baldwin’s rules see: Smith, M. B. Organic Synthesis; McGraw-Hill Inc.: New York, 1994; pp 601–611. 8. Prior to this time, these techniques were not utilized by undergraduates at Chico State. 9. All new compounds are consistent with spectral analyses and high-resolution mass spectroscopy.

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