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00:00:28 Born in Hong Kong in 1925, Koji Nakanishi received his Bachelor of Science degree in

00:00:34 1947.

00:00:36 He worked as a research fellow with Louis Fieser at Harvard University and received

00:00:42 his Ph.D. in 1954.

00:00:46 Since 1969, he has been professor of chemistry at Columbia University in New York City.

00:00:53 Dr. Nakanishi's most important contributions have been in the isolation and determination

00:00:58 of complex natural product cell structures.

00:01:02 He has also developed spectral techniques that elucidate the mode of action of many

00:01:07 of these natural compounds.

00:01:10 For example, his research in insect molting and insect hormones has led to the synthesis

00:01:16 of chemicals that can be used to retard insect feeding frenzies.

00:01:22 This can help stabilize agricultural products and reduce the potential for famine in many

00:01:28 third world countries.

00:01:30 His studies in the cell structure of ginkgo trees has led to the synthesis of products

00:01:35 with high medicinal value that are inexpensive to produce and distribute commercially.

00:01:43 Since the early 70s, Dr. Nakanishi has studied the cell structure of retinal proteins, an

00:01:49 important step in understanding the chemistry of vision.

00:01:53 He has continued to collaborate with scientists in a multidisciplinary approach, which, he

00:01:58 argues, necessitates a broader approach to the education of today's young scientists.

00:02:05 Dr. Nakanishi has published a wide variety of materials, including books on infrared

00:02:11 and circular dichroic spectroscopy, and articles on structures isolated from sweet potatoes,

00:02:19 cattail pollen, and even shark repellents found in fish secretions.

00:02:25 Joining Dr. Nakanishi for this interview is Dr. Leon B. Gortler, chairman of the Department

00:02:31 of Chemistry at Brooklyn College of the City University of New York.

00:02:36 Koji, I know that you were born in Hong Kong on May 11, 1925, but I know very little else

00:02:44 about your family and your growing up. Maybe you could tell me a little bit about, first,

00:02:50 how you came to be in Hong Kong in the first place.

00:02:52 I don't know. That's nothing to do. I was not born with this.

00:02:55 How did you happen to be born?

00:02:57 My father was in the, what is called now, he was in the banking business, which is now

00:03:01 called the Bank of Tokyo, and they are sent to many countries. And so he happened to be

00:03:08 in Hong Kong, and then I was born there. And then the next assignment was Lyon, and

00:03:16 then the next one is London, and next one in Alexandria. As a result, I was born in

00:03:21 Hong Kong, and then went to Lyon, stayed there for three, four years, London three, four

00:03:26 years, Alexandria three, four years, and then I came back. My parents came back to Japan

00:03:32 first time when I was about 13, 14 years old.

00:03:37 So when you returned to Japan, it was almost like going into a totally new culture.

00:03:43 Yes, yes.

00:03:43 And how was your schooling continued there?

00:03:46 Yeah, all sorts of funny things happened. I mean, I had to get a tutor, and teaching,

00:03:53 learning Japanese. I could not write a thing. And my mother, I remember, she got the texts,

00:04:01 the primary school texts, and she taught me how to write in Japanese on the boat way back

00:04:09 to Japan, you see. And then, well, I was more or less like a foreigner. One small instance,

00:04:18 which probably would be very funny for you people, is that I was on the beach. This is

00:04:24 nothing to do with chemistry, but I was wearing a crimson bathing suit, and I was laughed

00:04:32 at by all the other people. Look at that. He's wearing crimson. You see, in Japan, it

00:04:37 was pre-war. They all used, boys only wore black swimming suits, never crimson.

00:04:42 Ah, I see.

00:04:43 Yeah, I was ridiculed. I remember that, things like that.

00:04:47 And that was something you were not prepared for.

00:04:49 I had to get used to all sorts of things. As a result, I still don't understand the

00:04:57 subtle, some subtle aspects of Japanese culture. And I also don't understand the subtle aspects

00:05:06 of Western culture. So I'm one of those particular people who have no basis, neither West or

00:05:12 East.

00:05:13 At the end of your undergraduate work, you just went directly into graduate work, I take

00:05:19 it.

00:05:20 Well, yes, because at that time, there was no industry yet, you see. I mean, it has been

00:05:27 devastated. And so we just, and then the, it is the same today, too. The government

00:05:33 supported all the graduate students. So we didn't have any other place to go, so we just

00:05:38 automatically, in my case, stayed for the graduate school. And I went into, I joined

00:05:47 the biochemical group, who, the head was Professor Egami. He's a well-known biochemist. He's

00:05:56 unfortunately premature, he died. And then Professor Egami, and then his assistant professor

00:06:03 was Professor Hirata. And he's probably, well, he's the center of natural products, one of

00:06:11 the big centers of natural products.

00:06:13 In Japan.

00:06:14 In Japan. And quite a few famous people have come out of his school. And so Egami, and

00:06:21 then Professor Hirata. And I went more into, Hirata was, at that time, he was, I think

00:06:29 he was already starting to have an interest. This is in the late 40s, I think, starting

00:06:36 to have an interest about all these bioluminescence and things like that, you see, which is, I

00:06:40 think, quite amazing.

00:06:42 You essentially work with Hirata.

00:06:44 Yes.

00:06:45 And your first work was on actinomycins.

00:06:47 Yes.

00:06:47 And can you tell me just a little bit about that?

00:06:52 That is, actinomycin, as you know, is a peptide, and it's a very complicated structure. And

00:07:00 there was lots of interest in Japan already about antibiotics. Hirata later, he made lots

00:07:07 of contributions in antibiotics.

00:07:09 Tell me a little bit about your experiences at Harvard, working for Pfizer.

00:07:13 I don't think he exactly knew how to handle me. And eventually we became very close, and

00:07:20 I owed a tremendous amount to Pfizer. And I remember the first I called in, I went to

00:07:30 Harvard on a Saturday or Sunday, went up to his office, and he was there, typical Pfizer,

00:07:36 with a dirty lab coat and so on, doing experiments.

00:07:39 Yes, and the towel hanging.

00:07:41 Yes, towel, that's right. And he gave me a project. It was a synthesis of naftoquinone,

00:07:48 which is related to anti-malaria things. And he just gave me the project and sketched down

00:07:53 the reaction, do this, and that's it. And then I started working on this furiously.

00:08:02 And it was a so-called, you make a naftoquinone, and then with an alkyl chain, and there's

00:08:10 a so-called Foucault oxidation, which chops down the alkyl little by little. And I did

00:08:18 it. I don't know whether you know, but Pfizer wrote, after Foucault had died, he wrote,

00:08:23 I think he compiled all his papers and wrote it for Foucault. He assigned this to me.

00:08:30 And he didn't bother me for two, three months. Then he came back from a trip, and by this

00:08:37 time, I had done, because I knew about paper chromatography, you see, and when you're comparing

00:08:43 a series of naftoquinones with different side chains, paper chromatography is ideal. And

00:08:49 I did this time-wise in different time aliquots. And I got a beautiful set of spots, you see.

00:08:57 And I think Pfizer had not known about paper chromatography yet, at least it was not used

00:09:03 in his lab. So when he came back, he was astounded. And then he became, well, fortunate.

00:09:10 He made a whole difference in your relationship.

00:09:11 Yes, very fond of me. And then he was very kind to me. And it was only, he supported

00:09:19 me for the second year.

00:09:21 That's when your love affair with spectroscopy began.

00:09:24 Very fortunately, they had the second commercial automatic recording infrared made by Baird

00:09:32 Company. And I remember clearly that he did something, he put it in a cell, which means

00:09:38 I understand now. And he said, watch this, and there's a roll of paper, and then the

00:09:42 needle starts moving like this. And all of a sudden, at about 5.8 microns, so-called

00:09:48 now, it all of a sudden starts moving way down, and sharply goes up again, you see.

00:09:53 And he told me, you've got the ketoglue. And, well, I was dumbfounded. I didn't know

00:10:01 what the hell was happening. And, well, that turned out to be my first encounter with infrared.

00:10:07 I still have this chart with me.

00:10:10 And somehow, I got very interested in spectroscopy about that time. And the infrared was still

00:10:18 new, even at Harvard, for many people. And I think Woodward was, again, one of the pioneers

00:10:24 to use this. But anyhow, I started within the FISA, I went to FISA, okay, within the

00:10:29 FISA group, a small group, about six or seven of us. And we met every week, and had, you

00:10:37 know, a small gathering, introducing new papers in spectroscopy, including UV and infrared.

00:10:48 After five or six years at Tohoku, then it appeared as though it was time to move on

00:10:57 again. And you came to Columbia in 1969. How did that move come about? What prompted you

00:11:07 to leave Japan?

00:11:10 I don't know. Should I go through the episodes and things like that, or skip it? There was

00:11:15 some very unusual happenings.

00:11:16 That's a nice story, too, and you can tell it, at least for historical purposes. I think

00:11:23 it's enjoyable.

00:11:25 By the time I, in the late 60s, my group in Japan, I had a group of about 45, well-funded,

00:11:33 and so on. I had no reason to leave Japan, except that I was getting a little bit tireless,

00:11:39 because basically I don't like the Japanese hierarchical system.

00:11:44 One of the other spectroscopic techniques that you developed, or that you made great

00:11:50 use of, was circular dichroism.

00:11:53 The method that Harada and myself have developed, which we call the exciton chirality method,

00:11:59 is based on the coupled oscillator theory, which was developed in the 1930s. It's on

00:12:06 a firm, theoretical, non-empirical ground, and together with the bifurcate X-ray method,

00:12:16 which is for crystals, and our method, which we call the coupled oscillator method, or

00:12:21 the exciton chirality method, are the only two non-empirical methods in which one can

00:12:28 define the absolute configuration. There's an immense, I think, future for this.

00:12:35 I don't understand mathematics, so I'm also things like that, but when I say that I can

00:12:42 use it, it means that it's a very simple method.

00:12:44 You're not only known internationally as a chemist, and a very fine chemist, but you're

00:12:49 also well-known throughout the chemical community as a magician, and not even an amateur magician

00:12:56 anymore. People all over have been amazed by your feats. How did that start?

00:13:04 Yeah. I have one, this is when I was in the high teens. I have one card trick which still

00:13:12 no one has figured out, and I've only told it to my wife, and she thinks it's based on

00:13:18 such a stupid principle it's not going to work, but it's true, it's working. And that

00:13:25 of course, I perform this one card trick at parties, and my friends compliment, and

00:13:34 whenever you're complimented it tickles your ego, and then I start going more and more

00:13:38 into tricks, you see. And ever since I came to this, well, and then I started giving this

00:13:44 at parties, chemical parties, and then coming to the states and international meetings and

00:13:50 so on. And if you keep on pressed, and you have to add new things, and so as a result,

00:14:01 my repertoire now is quite broad. I cover a lot of things, including stage magics.

00:14:09 There's something you could show me.

00:14:11 Yeah, well I'll just show you. I don't always carry this.

00:14:20 This is, it's a new deck of cards, okay? I'm going to shuffle this now, and you can shuffle

00:14:28 this if you want. It's completely new. I just do one. Now I just want to just make sure

00:14:42 to get that out, and this one.

00:14:51 Now what do I do? You can now just take a card. You can take one or two cards. It doesn't

00:15:05 just take any card you want. Okay, well, wait a minute, don't do anything. Okay, I'll give

00:15:13 this back to you, and just put it back any place you want, and you can mix it up. Mix

00:15:22 it up. I'll do one more if we have time, but. Okay. Okay, give it to me, okay? I'll just

00:15:29 shuffle this. Okay, now what I've done is this is a new deck of cards, and I've taken

00:15:46 a card. No, you've taken a card. New deck of cards, I shuffled. You've taken a card,

00:15:53 and I've given you the remainder of the deck. You put it someplace, and you mixed it back

00:15:58 again, okay? Now, no, I don't think so. I'll use the other deck. I don't think. Sorry,

00:16:06 sometimes I don't have another deck. Where is it now? Here. I'll do it with this deck.

00:16:17 Okay, nothing, okay? What card did you pick up? Just tell me.

00:16:24 It was the five of spades. Okay, like this, okay? Watch. Okay, five of spades.

00:16:54 Okay, five of spades.

00:17:24 Okay, five of spades.