Publication

PSEUDO-PROLINES IN PEPTIDE-SYNTHESIS - DIRECT INSERTION OF SERINE AND THREONINE DERIVED OXAZOLIDINES IN DIPEPTIDES

1995
Journal Articles

Abstract

Dipeptides containing serine and threonine derived oxazolidines are prepared by reacting side chain unprotected dipeptides containing C-terminal Thr or Ser with dimethoxypropane. The resulting building blocks can be coupled in Fmoc-based solid phase peptide synthesis enhancing peptide solvation by its secondary structure disrupting potential. The present procedure may be considered as a first step towards a reversible modification of structural and functional properties of bioactive peptides and proteins.

Official source

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1995
Journal Articles

Abstract

Official source

Related concepts (15)

Protein secondary structure

Protein secondary structure is the local spatial conformation of the polypeptide backbone excluding the side chains. The two most common secondary structural elements are alpha helices and beta sheets, though beta turns and omega loops occur as well. Secondary structure elements typically spontaneously form as an intermediate before the protein folds into its three dimensional tertiary structure. Secondary structure is formally defined by the pattern of hydrogen bonds between the amino hydrogen and carboxyl oxygen atoms in the peptide backbone.

Peptide synthesis

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus).

Protein primary structure

Protein primary structure is the linear sequence of amino acids in a peptide or protein. By convention, the primary structure of a protein is reported starting from the amino-terminal (N) end to the carboxyl-terminal (C) end. Protein biosynthesis is most commonly performed by ribosomes in cells. Peptides can also be synthesized in the laboratory. Protein primary structures can be directly sequenced, or inferred from DNA sequencess.