Agnes Scott College

Dorothy Wrinch

Chemical Aspects of the Structure of Small Peptides: An Introduction
Munksgaard, Copenhagen Denmark, 1960

cover page

Table of Contents

  1. From the globular proteins to small peptides
    1. The problem of finding structures for the globular proteins
    2. Small peptides as today's focus in the organic chemical approach to peptide structure
    3. The cyclol structure for the peptide moiety of five ergot alkaloids
    4. The 'Asp.Lys' dipeptide containing a multiple peptide grouping
    5. Model molecules containing multiple peptide groupings
    6. Ideas of the amide and cyclol systems
  2. An organic chemical formulation of the amide and cyclol theories
    1. The amide hypothesis
    2. The cyclol hypothesis as a generalization of the amide hypothesis
    3. Characteristics of the multiple peptide groupings
    4. Forms assumed by the monomers in the amide and cyclol systems
    5. A comparison with the original formulation of the cyclol theory
    6. Hydrogen bridges within amide and cyclol structures
    7. Hydrogen bridge systems suggested by the cyclol hypothesis
    8. The two types of structure for peptides within the amide system
    9. The R-compositions and R-constitutions of polypeptide chains
    10. Degenerations of polypeptide chains and possible secondary syntheses
    11. Some peptides containing cyclol groupings, and their degenerations
    12. The significance of polypeptide chains as degradation products of peptides
    13. Some double α-monomers
    14. The α-imino acids obtained from peptides, and their homologues
    15. The α,ω monomers and ω- and ω,ω'-monomers obtained from peptides, and their homologues
    16. The extended amide hypothesis and branched polypeptide chains
    17. Amide groupings containing C-N bonds of the four different kinds
    18. The extended cyclol hypothesis in parallel with the extended amide hypothesis
    19. Some structural fragments in α,ω-peptides
    20. Imbalances of α- and ω-NH2 groups and α- and ω-COOH groups in peptides
    21. The varying interpretations of data afforded b the amide and cyclol systems
    22. Some structural features of bacitracin A
    23. A branch point at the phenylalanine monomer?
    24. The bonds uniting the lysine and aspartic acid monomers
    25. The generalized peptide groupings in a wider context
    26. The special character of the two-bond peptide groupings
    27. Amine and carboxyl transfers
    28. Two-bond peptide groupings as intermediates in certain enzymic reactions?
    29. Other two-bond groupings as intermediates in some enzymic reactions
    30. The 'non-peptide' grouping in gramicidin
    31. How can labile groupings be stabilized
    32. The place in organic chemistry of the multiple peptide groupings
      Appendix A. Certain ortho groupings and related multiple groupings
      Appendix B. Excerpts from the Works of Emil Fischer
  3. Structures for small peptides within the amide and cyclol systems
    1. Introduction
    2. Structure types for small α-peptides
    3. Some structure types for tripeptides
    4. Some structure types for tetrapeptides
    5. Degeneration products of tripeptides and tetrapeptides
    6. Certain issues introduced by the cyclol structures
    7. Some general considerations
    8. A few structure types for pentapeptides
    9. Intermolecular proton migrations and the formation of larger peptides
    10. Some hydrogen-bridged dimers and trimers and other oligomers
    11. The R-compositions and R-constitutions of a peptide with a structure of given type
    12. The bearing of the R-constitutions of peptides on routes of degeneration
    13. The embedding of a hydantoin or piperazine ring in peptide structures
    14. On the significance of degradation products containing hydantoin or piperazine rings
    15. The history of the ergot tripeptide structure
    16. The occasion for the new structure
    17. The reductive cleavage of the tripeptides
    18. The investigation of the tripeptides by high temperature cleavage
    19. The conditioned stability of the new structure
    20. Stabilizing factors in the tripeptide structures
    21. Limitations in hydrolytic degradation studies
    22. Determining the L- or D-forms of the monomers in peptides
    23. A change in chemical constitution or a superposed 'fine structure'?
  4. Growing points in peptides studies
    1. Introduction
    2. Peptides as an expression of the nature of their monomers
    3. The broader viewpoint regarding peptide groupings
    4. Other issues
    5. Developments suggested by the researches on the ergot tripeptides
    6. Double α-monomers and the penicillin structures
    7. The trend towards structures of higher connexity
    8. Model molecules suggested by 'Asp.Lys'
    9. The bearing of 'Asp.Lys' on the structure of bacitracin A
    10. A polycyclic structure for bacitracin A?
    11. 'Asp.Lys' as one of a set of α,ω-dipeptides
    12. Towards the synthesis of multiple peptide groupings by transannular interactions