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Synthesis

Podcast: Sarah Reisman and Melanie Sanford on how organic chemistry is changing and how they’ve learned to choose priorities

Two organic-chemistry powerhouses tell Stereo Chemistry about how they find research inspiration and what organic chemistry means to them

by Leigh Krietsch Boerner , Kerri Jansen
February 15, 2022

 

Graphic with the words "In conversation with Sarah Reisman and Melanie Sanford" next to halftone images of the two chemists.
Credit: Will Ludwig/C&EN/Lance Hayashida/University of Michigan
Credit: C&EN

Being a chemistry professor is a juggling act. But sometimes professors have too many balls in the air. How do they know which ones to grab and which to let drop? In this episode of Stereo Chemistry, C&EN associate editor Leigh Krietsch Boerner sits down with organic chemists Sarah Reisman and Melanie Sanford to hear how they decide what projects to work on, what sparks joy for them in the lab, and what being an organic chemist really means to them.

Sign up for C&EN’s Selling Your Science: The Art of Science Communication at cenm.ag/sciencecommunication.

Read more about Sarah:

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Read more about Melanie:

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Subscribe to Stereo Chemistry now on Apple Podcasts, Spotify, or wherever you get your podcasts.

The following is a transcript of the episode. Interviews have been edited for length and clarity.

Sarah Reisman: I was like wishing I had a time machine, and I could go back to myself and like, punch myself in the face, actually. It wasn’t even like say no, it was like, physically remind myself that I didn’t like to do that.

Kerri Jansen: That was organic chemist Sarah Reisman on the subtle way she sometimes wants to remind herself not to take on tasks she doesn’t enjoy.

Attabey Rodríguez Benítez: Everybody has to deal with things they don’t want to do at work. Chemistry professors have a little bit of freedom on what projects they choose to work on; the flip side is that they also have to deal with a lot of outside pressure on what those projects should be.

Kerri: In this episode of Stereo Chemistry, we’re hearing from two powerhouse professors of organic chemistry: Sarah Reisman at the California Institute of Technology and Melanie Sanford at the University of Michigan. I’m Kerri Jansen.

Attabey: And I’m Attabey Rodríguez Benítez.

Kerri: Sarah and Melanie recently sat down with C&EN associate editor Leigh Krietsch Boerner to discuss making your life as an organic chemist the one you want, and how to enjoy both the journey and the destination.

Kerri: Welcome to the show Leigh!

Leigh: Thanks, it’s lovely to be here once again. I’m last this season!

Kerri: Yes! This episode is the final installment in our current series. Make sure you stick around until the end of the episode to hear what’s up next for Stereo Chemistry.

Leigh: I’m bringing the champagne.

Attabey: Well, before we pop the bubbly, we have a lot of great stuff to share from Sarah and Melanie. So, Leigh, why did you want to get these two together in the first place?

Leigh: Well, Melanie and Sarah have a lot in common in that they’re both organic chemistry professors. But they do different flavors of organic chemistry. Melanie leans more organometallic, which involves molecules that have both metal atoms and carbon atoms, like you would normally find in an organic molecule. She works on a lot of different projects involving catalysts, such as C-H functionalization and fluorination chemistry. And while Sarah also plays with catalysis chemistry, she’s mostly known for doing total synthesis of natural products.

Kerri: Natural products . . . so that’s making these crazy complex molecules that are only found in nature, right?

Leigh: Right, only found in nature in very small amounts and that have some property that could make them potential drugs, or antibiotics, or other valuable bioactive molecules. Some organic chemists want to find ways to make these molecules in larger amounts so they can study their properties.

Attabey: So even though they’re both considered organic chemists, their research is pretty different.

Leigh: Yeah! And there are some other ways in which their research diverges, which we’ll talk more about later. But they have a lot of overlap, too. The world of organic chemistry is not huge, and, still, in 2022, there are not many women in the discipline. So, yeah, they’ve known each other for a while. During our interview, I asked them if they could remember when they met. Melanie answered first.

Melanie Sanford: I don’t know if it’s the first time we met. But my most distinctive early memory of Sarah is when we interviewed her for a position here at Michigan. What I remember most distinctly is when she came back for her second visit, and there was like a little dinner party. And, you know, I remember talking to Sarah and trying to convince her to come to Michigan. And I also remember that it was like late January, early February of 2008. And my son had been born like a month earlier. And I was like, fried. I mean, I think it was the first event that I actually left the house for since he was born. And so I just remember being so overwhelmed with everything but yet really wanting Sarah to come and so trying to convince her, but being completely frazzled at the same time.

Sarah Reisman: Yeah, I was gonna say I also thought it was when I interviewed at Michigan and remember actually you being quite pregnant when I interviewed and having had the child, you know, between when I initially interviewed and then when I returned. And I think for me, what I remember actually is when Melanie came to visit Yale when I was a graduate student. And it was when you were, I think interviewing for jobs yourself at that point. And I remember seeing your job talk at Yale.

Melanie Sanford: Yeah, no I remember that interview at Yale. And I mean, I was an undergraduate there, right, so I remember that very clearly. Because it was like every meeting was with a faculty member that I’d had for like a class or, you know, had been a mentor in some way. And so it was super intimidating. I remember the proposal presentation, I was like, it’s going to be so stressful. I need to figure out a way to make it less stressful. So I said to them at the beginning of it, I said, “You know, I know you guys are going to ask me a lot of questions. And I’m probably not going to know some of the answers. So you guys can just all remember that, when I don’t know the answer, it’s actually, you know, your fault.” There was like, silence. And then they were like, ho ho ho ho ho. And I was like, oh, phew. At least my joke didn’t bomb.

Kerri: As we know now, Melanie decided to take her burgeoning comic career to Michigan, rather than Yale, and Sarah chose Caltech when it was her turn. But both have been running their own labs for many years now.

Leigh: Right, and like most professors, they have to manage a lot of different aspects of their jobs at the same time—their research, their students, teaching, writing grants, writing papers, and so many other things.

Personally, I am crap at keeping a bunch of balls in the air at once, I’d be dropping them constantly.

Attabey: And you’re not alone in that, Leigh; even very successful chemistry professors like Melanie and Sarah drop some from time to time.

Leigh: Yeah, and that’s something I asked them about. I wanted to hear how they manage priorities and deal with setbacks.

Leigh (in interview): Well, how do you get out of that, then when you feel like you’re failing? How do you kind of boost yourself back up? How do you keep going?

Sarah Reisman: Compartmentalization? [laughter]

Melanie Sanford: Exactly!

Sarah Reisman: There are more tasks to do than there are time to do them.

Melanie Sanford: Yep.

Sarah Reisman: And the good thing about that is that, it means that you don’t have too much time to dwell on the things that are not going well, you just move on to the next, and then circle back. At the end of the day, there’s always something still to be done. And I think at some level, I have learned how to just, you know, forgive myself . . .

Melanie Sanford: Right. Let it go!

Sarah Reisman: . . . for not maybe doing things quite as quickly as I want to. And then it gets me thinking about, what things can I do with my lab so that papers come in at a stage where they can get turned around more quickly? How do we take general lessons and, say, make sure that our first draft that comes to me hits at a level where there’s less back and forth going on? Or what can I do to make sure we’re running the right experiments? Because I definitely feel like every year I am learning how to do this job better and, you know, there are times where I start to feel frustrated. And then I’m like, well, what can I do, you know, what proactive measure can I take, so that this doesn’t happen next time.

Melanie Sanford: Totally. So I guess my question is, how do you decide what to say yes to? What goes into you making a decision about that?

Sarah Reisman: Well, I think for a long time, as I’m sure was true for you probably at some part in your career, you say yes to just about everything

Melanie Sanford: Exactly, right, yeah.

Sarah Reisman: You’re like, well, A, you’re getting asked, and how do you say no. And so I’ve started to try and be more selective in the last several years. And I think it, it gets easier to start saying no, once you feel like, honestly, at capacity, right?

Somebody reminded me that you don’t want to say no to things that you like, just because you feel too busy. And that it’s more important to say no to things that are not rewarding. And so I’m trying to prioritize a few things like related to, say, women in chemistry, or diversity, equity, inclusion more generally. I do think those are important and rewarding if you’re on the right kind of committee that can make changes. But I’m less interested in being on a committee just because they were looking for one more person that fits a certain demographic to be there. And if I don’t think it’s actually going to, you know, there’s no power to that committee, or there’s no like, action item that it feels like is gonna get done. I think I still need to say no more often.

Melanie Sanford: For sure. Yeah.

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Sarah Reisman: I feel like my lessons learned are, when I have said yes, and then after like a year, I’m like, oh my gosh, what am I doing? I hate this task. Then I sort of write that down as a thing that I want to make sure I don’t say yes to again, that type of committee or commitment.

Melanie Sanford: One thing I really like is to be on committees where my voice will be different than the rest of the people. And when I can say something that makes people look at something from a different perspective, or convince them that this assistant professor, for example, is actually doing really great stuff, and have them elevate that person, and ultimately, they win an award. That to me is really cool. So I try to be on things where I feel like I can be an effective advocate, because that’s where you can really make a difference, I would say. Attabey: For a lot of us, learning what to prioritize and what to let go is an ongoing journey. Figuring out what to say yes to is a big part of how both Sarah and Melanie steer their careers into territory they find rewarding.

Leigh: Yeah, and I was really curious about what fires them up, research-wise. And they each had a different answer to that question, in a way that kind of reveals another important way their work differs in focus. Let me see if I can explain. Attabey, you like to bake, right?

Attabey: Yeah, another pandemic hobby I acquired. Why?

Leigh: When you bake, which part do you most enjoy—the actual act of baking, like combining the ingredients, or whatever baked good comes out at the end?

Attabey: Well, I like what I get at the end, when it tastes good, that is. But I think I like the process itself a little bit more. For example, I really love the process of maintaining a sourdough starter. Although it’s funny how even if that process is simple, just adding water, we can still mess it up. Ask my recently deceased sourdough starter . . .

Leigh: OK, so you’re mainly a process baker. I also like to bake, but I’m more interested in my product, like what tasty things I get out after it’s all done. So I am the nine millionth person to compare chemistry to baking, but chemists fall into these process vs. product categories too. For Melanie, what she makes is important, but how she gets there is what she really focuses on. She’s a process chemist. Sarah is the opposite—she told us she definitely appreciates the process of synthesizing molecules, but at the end of the day, she’s most concerned about what’s coming out at the end. She’s a product chemist, also known as a target-directed chemist.

Attabey: Got it. So Melanie likes baking the bread, but Sarah is more focused on the finished loaf.

Leigh: Exactly.

Kerri: OK, so now that we’ve stretched this analogy to its breaking point, Leigh, let’s go back to your question about where Sarah and Melanie find their research inspiration.

Leigh: Right. You can get a sense of the different approaches each of them takes from the way they talk about their work. Here’s Sarah.

Sarah Reisman: I will say my favorite thing in a project is when we have a plan for a synthesis, and there’s something unexpected that happens. And then we can use it effectively, like we can actually make our approach shorter because of this unexpected discovery or rearrangement or something like that. And then you’re like, oh, that solves our problem. And we can take advantage of this and sort of develop it in a creative way that we didn’t expect. And it takes a special student who can, like, recognize that and not just get disappointed but see that the unexpected is actually a better direction to go.

Melanie Sanford: I would totally piggyback on that, it’s almost exactly the same thing, except the reason that I like not doing target-directed synthesis is because my favorite part of research is when something unexpected happens that’s way more interesting than what you are starting you are trying to do originally. And then because you don’t really care what you’re trying to make at the end of the day, you could just do that. And it’s even more awesome, you know. So I think that for me, that’s what would be hard about doing what Sarah does is like, at the end of the day, you still . . . you want to make your molecule and I’m so easily distracted. And I think something is cool, and I want to pursue that. And so for me, it’s like getting back to the target would be very difficult.

Leigh (in interview): How did you each get interested in the fields that you’re in now?

Sarah Reisman: You know, for me, I’ve always just been drawn to these types of structures and molecules, just wanting to think about how you put them together. I see a structure and I just start thinking about like, how do you make this, how do you . . . what bonds should you be trying to make? What types of reactions can you think about, from a strategy level?

Melanie Sanford: For me, I saw organic chemistry as sort of a series of like, very well defined rules. And I think what attracted me to organometallic chemistry is I was like, these metals are amazing! They can do anything! You know, there’s no rules, or at least the rules, like I don’t understand them, and I want to, you know? So I guess for me, it was more like the wonder of going through organic chemistry and seeing how everything—of course, it wasn’t, but as an undergraduate seemed like—totally worked out. Like everyone knew exactly how things were gonna react and where the arrows went. And then you get to organometallic chemistry, and it just, like, blew my mind that these crazy things could happen, and you just never knew what to expect. And so for me, that’s what sort of set me on the path to thinking about metals and organometallic chemistry.

Leigh (in interview): It seems like that would scare a lot of people off, though, like all of a sudden, look at all these d orbitals. And there’s f orbitals, just like all this crazy stuff that can go on.

Melanie Sanford: But so I guess the way I looked at it was more like anything could happen. Like you could put these reactants in and anything could happen because there’s d and f orbitals. It almost seemed like you could never predict, or at least something could happen and you would just be totally blown away and never have expected it. And to me that’s like the discovery component of science that I thought was really cool.

Leigh (in studio): As you can hear, Melanie is pretty excited about metals. And that’s, in part, because of her background, which is a bit off the expected reaction pathway for an organic chemist, so to speak.

Melanie Sanford: So my PhD from Caltech is actually in inorganic chemistry. So I guess I have always felt a little bit like an outsider, maybe, in the field of organic chemistry. When I was applying for jobs, I thought I would just apply for inorganic jobs. And then I was really surprised when people sort of viewed me as an organic chemist. I always hear people say that organic chemistry isn’t that inclusive of a field. But actually, at least in terms of the sort of research component, I felt that I was embraced by organic chemists almost more than by inorganic chemists when I first entered my independent career.

Attabey: Well, does it really matter if Melanie doesn’t have the same background as most organic chemists? Would other organic chemists view her work differently because of it?

Leigh: Yes and no? It used to matter. But according to Melanie and Sarah, that’s not so much the case anymore.

Kerri: Next up, we’ll hear Melanie and Sarah’s thoughts on what organic chemistry is, and how that field may be changing. That’s after a short break.

Arminda Downey-Mavromatis: Hello, Arminda Downey-Mavromatis here! I work with C&EN’s Audience Engagement team, and I am thrilled to tell you about our latest newsletter, Selling Your Science: The Art of Science Communication.

Honestly, science communication is the job of every scientist. Over the course of your career, you’ll need to be able to speak about your science to a wide variety of audiences outside of your specific area of research.

Every Thursday, over the course of 6 weeks, we’ll send you advice from one of our guest hosts on topics including how to sell your science to your friends and family, how to create an engaging research poster, how to give an engaging research talk, how to get your science in front of journalists, how to win research funding, and how to create a website to showcase your work.

You can sign up now at cenm.ag/sciencecommunication. Again, you can sign up for C&EN’s Selling Your Science: The Art of Science Communication at cenm.ag/sciencecommunication. We’ll include that link in the show notes on C&EN’s website.

And now, back to the show.

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Kerri: In the first part of the episode, Melanie and Sarah talked about why they got into science and how they approach setting priorities. Next, we’ll pull back a little bit and look at the field of organic chemistry overall—what the field was, and is, and what it might be turning into.

Attabey: So our discussion touched on a big question for some chemists today: What is organic chemistry?

Leigh: If you ask 100 chemists that, you’ll get 100 different answers. For some people, an organic chemist should be able to rattle off all the big named reactions, while others challenge the emphasis on name reactions, and argue for different ways to measure competence. But Melanie and Sarah told me that they think this thing we call organic chemistry is going through a bit of a makeover.

Leigh (in interview): So you know, you mentioned that organic chemistry has not been, you know, super inclusive in a research way. Do you think that’s changed?

Melanie Sanford: Organic chemistry has a reputation. I mean, I guess my perspective was that I never took a synthesis class. I didn’t know all the named reactions, I still don’t know most of the named reactions. And so I just felt like organic chemists would just look at me and be like you’re not a real organic chemist. I guess, I don’t usually tell them that I don’t know all the named reactions, so maybe they just don’t know, you know. But I found that people were really welcoming. And they thought that I was bringing something different to the field and that it was valuable. It’s just not what I had expected. But I guess I just realized that a lot of organic chemists at least have a pretty broad view of the field and what organic chemistry is and what interesting contributions to it can be. So I don’t know what Sarah thinks about that. Because she’s positioned differently relative to the field.

Sarah Reisman: I guess I would say, I do think that there are a lot of reputations about organic chemists that I think . . . I like to think predate us, you know, and about synthesis and how people connected or valued different contributions within organic chemistry. And I do feel like there’s less of a “this is an organic chemist,” right? That this flavor of organic chemistry is the only flavor. I think, you know, people have moved in different directions. And I think that’s a good thing. And maybe it’s because we have to start branching out, right? It’s like you have to keep moving the field forward. And I think that requires sometimes looking at other disciplines and the types of tools they’re developing and asking how do you bring that into organic chemistry, or asking what kind of problems are they solving that we are uniquely set up to do? That’s how we continue to do interesting chemistry, I think. So I’d like to think that it is broadening terms of the definition of what’s organic chemistry. Or maybe it’s just not important that it’s like everyone has their . . . gets stamped as a card-carrying organic chemist or not, I don’t know.

Melanie Sanford: My sense is that pharma is actually helping with this lately. I mean, when I started my career, they would invite me for a seminar, we’d have a really nice day, they’d ask me all these questions about all my reactions, right? And then at the end of the day would tell me, “We would never hire one of your students without a postdoc.” Because even though they were very interested in what I was telling them all day, they were like, well, that person really needs to have done more synthesis, you know, before we would hire them. And I feel like now, they are recognizing in a way that I think is really great, that like having people with different perspectives actually is super valuable to the overall enterprise, you know, and that everyone having training in total synthesis, maybe isn’t the best way to go. Certainly you need those people. And you also need people that know how to do catalysis or know how to do various different kinds of things. So I think that’s been good. And something that has certainly changed during my time in the field.

Leigh (in interview): Why do you think that’s changed? Like what set that off?

Sarah Reisman: Part of it is that I’m, in some ways, because of this sort of constant migration of catalysis, and organometallics and different types of chemistries into the arsenal of the organic chemist, right, that, it can be really helpful to have chemists with expertise in different areas, right, and just realizing that if you are going to be using the most modern methods, let’s say, to make a molecule, then having people who were involved in the development of that chemistry can be really helpful, right. And that’s not just coming out of one group, right, that’s coming out of lots of different labs.

Melanie Sanford: Yeah.Sarah Reisman: So it comes back to this idea that they want to have a team of people who think about a problem from different perspectives.

Leigh (in studio): As Sarah and Melanie see it, this shift means that the chemistry community is more likely to produce good products, and have a good time getting there.

Kerri: And if we all can figure out how to set healthy boundaries, we’ll really be making progress.

Attabey: Right. And I hope listeners can find some takeaways in what they shared about managing priorities, even for those of us who aren’t managing an organic chemistry lab. That’s definitely one of my own goals for this year, to not say yes to everything! Maybe then I’ll finally have some time to really nail my sourdough. And maybe bring it back to life, maybe?

Kerri: Something we can all aspire to. You can read more about the exciting work coming out of Sarah’s and Melanie’s labs on C&EN’s website, cen.acs.org. We’ll link to some stories featuring them in this episode’s show notes on our website.

Attabey: Kerri, didn’t you say you had a message for our listeners about what’s coming up next on Stereo Chemistry?

Logo for C&EN's Bonding Time with the words C&EN's Bonding Time layered on top of two bonded aromatic rings.
Credit: Will Ludwig/C&EN

Kerri: I do, yes. As we mentioned, this episode is the fourth and final installment in our current series, which features sensational chemists in conversation with each other. We heard from you that you love this style of episode, and frankly, we like making them, so we’ll definitely have more episodes like this coming your way in the future. We even came up with a special name for them. We’re calling them “C&EN’s Bonding Time.”

Attabey: Of course it’s a chemistry pun. Because of course it is.

Kerri: You’ll still find those episodes right here in your Stereo Chemistry feed. Kind of a show within a show. If you’d like to suggest a sensational chemist, or two, to be featured in C&EN’s Bonding Time, let us know by emailing cenfeedback@acs.org. We’ll have more details for you on those upcoming episodes soon.

First, however, we have a different story to tell. The next season of Stereo Chemistry will explore the future of water. What does that mean? Well, C&EN’s reporters are digging into that question at this very moment. And we would also like to know what questions you have about the future of water. No question is too big or too small. Again, you can email us at cenfeedback@acs.org. Our contact info is included in the episode’s show notes as well.

Attabey: And while you’re waiting on new episodes, you can whet your palate by revisiting our episode from this season with environmental engineers Jessica Ray and William Tarpeh. We heard how they’re thinking about the future of clean water, and they also shared how they’ve learned to thrive as assistant professors.

Kerri: Thanks for listening, and we’ll see you soon.

Attabey: This episode was written by Leigh Krietsch Boerner and produced by Kerri Jansen. Story editing by Michael Torrice and Amanda Yarnell. Production assistance from Gina Vitale.

Kerri: The music in this episode was “A Train on a River” by Dialgo and “Different Kind of Love — Instrumental Version” by Anthony Lazaro. The promo music was “Plain Loafer” by Kevin MacLeod.

Attabey:Stereo Chemistry is the official podcast of Chemical & Engineering News. C&EN is an independent news outlet published by the American Chemical Society. Thanks for listening.

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