V. V. Suresh Babu

Synthesis of β-Amino Acids: 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TBTU) for Activation of Fmoc-/Boc-/Z-α-Amino Acids

Abstract A new and efficient method for the homologation of urethane protected α-amino acids to its β-homomers by the Arndt-Eistert method using TBTU as a coupling agent is described. Several Fmoc-/Boc-/Z-protected α-amino diazoketone derivatives have been obtained as crystalline solids in good yield. The method is found to be rapid and stereospecific.

One hundred years of peptide chemistry

Emil Fischer is considered to be the founding father of the field of peptide chemistry and originator of the term peptide. In the beginning of the 20th century, Fischer had a clear vision to foresee the day when a protein would be synthesized. Subsequent to this brilliant beginning, progress however was slow for the next 50 years. In 1953, the chemical synthesis of oxytocin by duVigneaud was a landmark achievement. The subsequent decades witnessed the discovery of a vast number of biologically active peptides. The last three decades saw development of multiple simultaneous syntheses, peptide libraries and peptide vaccines. This article is a concise account of the types of peptides discovered and their biological role.

Improved solid phase synthesis of luteinizing hormone releasing hormone analogues using 9-fluorenylmethyloxycarbonyl amino acid active esters and catalytic transfer hydrogenation with minimal side-chain protection and their biological activities

Using mainly 9-fluorenylmethyloxycarbonyl amino acid 2, 4, 5-trichlorophenyl esters in the presence of 1-hydroxybenzotriazole and the solid supportp-alkoxybenzyl alcohol resin, synthesis of luteinizing hormone releasing hormone analogues was carried out with minimal side-chain protection. Catalytic transfer hydrogenation was employed for removal of NO2 and Z-groups from Arg and < Glu respectively avoiding the use of HF and this led to good yields. An aromatic, hydrophilic amino acid, D-(p-hydroxyphenyl) glycine was incorporated into luteinizing hormone releasing hormone molecule along with other modifications. The agonistic as well as antagonistic activities of all the peptides have been studied

Fmoc-Peptide Acid Chlorides in Fragment Coupling: Synthesis of β-Casomorphin by 3+2 Divergent Approach

Abstract Fmoc-peptide acid chlorides are prepared and used as rapid and efficient coupling agents in fragment coupling. Thus the synthesis of the model tetrapeptide Leu-Ala-Gly-Val and P-casomorhin (Tyr-Pro-Phe-Pro-Gly) are accomplished by the (2+2) and (3+2) divergent approach respectively.

Quinoline-Thioureidopeptides: A New Approach for the Synthesis of Quinoline-Isothiocyanate and Their Peptide Linkage

We present an efficient synthetic route for quinoline condensed thioureidopeptidyl esters from corresponding isothiocyanate and amino acid esters. The utility of quinoline isothiocyanate as major building block for desired thioureidopeptides of quinoline interests, with good yield with excellent purity. All the new compounds are well characterized by IR, 1H NMR, mass and elemental analysis data.

tert-Butyl 4,4-dimethyl-5-oxo-1,3-oxazolidine-3-carboxyl­ate

In the title compound, C10H17NO4 the urethane group is planar and the oxazolidinone ring adopts an envelope conformation. Intermolecular C-H·O interactions link the screw- and glide-related molecules into a two-dimensional network parallel to (101).