Chemistry of Insulin. Based on Chemistry of Insulin by F. Sanger, Science 129, (1959)

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1 Chemistry of Insulin Based on Chemistry of Insulin by F. Sanger, Science 129, (1959)

2 Human Insulin

3 The Sanger Method The DNP- amino acids are bright yellow substances and can be separated from the unsubs;tuted amino acids by extrac;on with ether. They could be frac;onated by par;;on chromatogra- phy, a method which had just been introduced by Gordon, Mar;n, and Synge (6) at that ;me. The DNP- amino acids could then be iden;fied by comparison of their chromatographic rates with those of synthe;c DNP- deriva;ves.

4 End Group Analysis of Insulin O 2 N NO 2 NH NO 2 O 2 N N H OH Insulin 1) DNP- F 2) Complete Acid hydrolysis DNP-Phe O + H 3 N ε-dnp-lys O O NO 2 O 2 N N H O OH And other Amino acids DNP-Gly

5 OxidaTon of Insulin A- chain B- chain

6 ParTal Hydrolysis The N- terminus of the B- chain is: Phe- Val- Asp- Glu

7 A- chain The main technical problem was the frac;ona;on of the extremely complex mixtures that resulted from par;al hydrolysis of a protein. However, Consden, Gordon, Mar;n and Synge (9) had shown that small pep;des could be well frac;onated by paper chromatography and had determined the sequence in the pentapep;de gramicidin S from the com- posi;on of pep;des produced on acid hydrolysis. The N- terminus of the A- chain was similarly determined to be: Gly- Ile- Val- Glu- Glu

8 Sequence of the B- Chain Since the mixture was too complex for direct analysis by paper chromatography it was necessary to carry out certain preliminary group separa;ons in order to obtain frac;ons containing five to 20 pep;des that could then be separated on paper. This was accomplished by ionophoresis, ion ex- change chromatography, and adsorp;on on charcoal. These simplified mixtures were then frac;onated by two- dimen- sional paper chromatography. The pep- ;de spots were cut out, and the material was eluted from the paper, subjected to complete hydrolysis, and analyzed for its cons;tuent amino acids.

9 Sequence of the B- Chain In this way about 45 pep;des were iden;fied in various frac;ons of the par- ;al acid hydrolyzate, and the following five sequences were deduced as being present in the phenylalanine chain: These five sequences contain all but four of the amino acid residues of frac;on B. It was not possible to determine from the small pep;des derived from acid hydrolyzates the posi;on of the remaining four residues or the manner in which the five sequences given above were joined together.

10 EnzymaTc Hydrolysis Proteoly;c enzymes are much more specific than is acid, since only a few of the pep;de bonds are suscep;ble. They give rise to larger pep;des, which in general are more difficult to frac;on- ate by paper chromatography. However, there are rela;vely few of them, so the mixtures are less complex. As an example we may consider a pep;de Bp3 obtained by the ac;on of pepsin. It had the following composi;on: Bp3: Phe(CySO3H, Asp, Glu, Ser, Gly, Val, Leu, His) Of these components the most important are aspar;c acid and serine, since they occur only once in the chain. Aspar;c acid is present only in the N- terminal sequence (1), and serine is in sequence 5. (1) All of sequence 1 and at least the N- terminal part of sequence 5 are present in pep;de Bp3. (2) None of the other sequences are present follows from the fact that Bp3 contains no arginine (sequence 2); threonine, proline, or lysine (sequence 3); or tyrosine (sequence 4).

11 Sequence of B- chain Sequence 1 Sequence 5 Sequence 4 Phe- Val- Asp- Glu- His- Leu- CySO3H- Gly- Ser- His- Leu- Val- Glu- Ala- Leu- Tyr- Leu- Val- CySO3H- Gly- Glu- Arg- Gly- Phe- Phe- Tyr- Thr- Pro- Lys- Ala Sequence 2 Sequence 3

12 Sequence of A- chain Essen;ally similar methods were used to determine the sequence of frac;on A (12). Although it was the shorter of the two chains, the determina;on of its structure was more difficult. Considerable difficulty was at first experienced with the cysteic acid pep;des. Frac;on A contains the sequence CySO3H- CySO3H and this gave rise to a number of pep;des which were very soluble in water and which would not frac;onate easily by paper chromatography. Gly- Ileu- Val- Glu- Glu- CySOaH- CySOsH- Ala- Ser- Val- CySOsH- Ser- Leu- Tyr- Glu- Leu- Glu- Asp- Tyr- CySOsH- Asp

13 Arrangement of Disulfide Bridges In order to determine the distribu;on of the disulfide bridges, it was necessary to isolate, from unoxidized insulin, pep- ;des containing intact cys;ne residues. These could then be oxidized to give cys- teic acid pep;des, which could be recognized since they had been found in the hydrolyzates of the oxidized chains. However, an unexpected difficulty arose in that, during hydrolysis, a reac;on occurred which caused a random rearrangement of the disulfide bonds, so that cys;ne pep;des were isolated which were not actual fragments of the original insulin, and it would have appeared from the results that every half- cys;ne was combined to every other half- cys;ne residue. It was found that there were two types of disulfide interchange reac;ons (14). One took place in neutral and alkaline solu;on and was catalyzed by - SH compounds.

14 By Using SH Inhibitors.. A pep;de was obtained which on oxida;on gave the two cysteic acid pep;des CySO3H- Asp- NH2 and Leu- Val- CySOsH- Gly- Glu- Arg- Gly- Phe- Phe

15 The Insulin Sequence

16 Insulin from Different Species All the results given above were ob- tained on insulin from ca_le. When in- sulins from four other species were stud- ied by essen;ally the same methods, it was found that the whole of the B chain was iden;cal in all species, and the only differences that were found in the three amino acids contained within the disulfide ring of the A chain, which in the ca_le are Ala- Ser- Val and in the other species are as follows: Pig, Thr- Ser- Ileu Sheep, Ala- Gly- Val Horse, Thr- Gly- Ileu Whale, Thr- Ser- Ileu

17 The Final Words The determina;on of the structure of insulin clearly opens up the way to similar studies on other proteins, and already such studies are going on in a number of laboratories. These studies are aimed at determining the exact chemical structure of the many proteins that go to make up living ma_er and hence at understanding how these proteins perform their specific func;ons on which the processes of life depend. One may also hope that studies on proteins may reveal changes that take place in disease, and that our efforts may be of more prac;cal use to humanity. Fredrick Sanger won the Nobel Prize in Chemistry TWICE For his work on the structure of proteins, especially that of Insulin (shared with Gilbert) For their contributons concerning the DeterminaTon of base sequences of nucleic acids.

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