Beta-amino acids and beta-homo amino acids have related structures. In both, the amino group is attached to the second carbon atom from the acid group. The difference is in the carbon skeleton. Beta-amino acids have the same carbon skeleton as alpha-amino acids, except the amine group is attached to a different carbon. The carbon skeletons of beta-homo amino acids have an extra methylene group following the primary acid group.
Some products can plausibly have two names, one based on beta-amino acid nomenclature and another based on beta-homo amino acid nomenclature. Beta-leucine, for instance, can also be named beta-homovaline.
Few beta-amino acids occur naturally in peptides. The most common ones are beta-alanine, beta-phenylalanine and beta tyrosine. Beta-alanine is found in the dipeptides carnosine and anserine. Carnosine buffers acid buildup in muscle and is reported to decrease fatigue in athletes. Anserine can improve memory loss in mouse models of Altzheimer’s disease. Both dipeptides chelate metals and may have antioxidant properties. The dipeptide acetyl-glycyl-beta-alanine is used commercially in skin care products for whitening skin spots.
Beta-phenylalanine and beta-tyrosine are two other beta-amino acids that occur in some naturally occuring peptides. Many of these peptides have interesting biological activity, ranging from antimicrobial to insecticidal.
Beta-homo amino acids are homologs of standard amino acids that are prepared synthetically. Incorporating them into peptides helps to improve resistance to peptidases. Therefore beta-amino and beta-homoamino acids are of interest in developing peptide pharmaceuticals.
AAPPTec provides a large variety of high-purity, competitively priced beta-amino and beta-homo amino acid derivatives for peptide synthesis.