Diamino acid

In chemistry, a diamino acid, also called a diamino carboxylic acid, is a molecule containing at least one carboxyl and two amine functional groups. Diamino acids belong to the class of amino acids.

Biochemical function

Asparagine, glutamine and lysine are proteinaceous diamino acids which are components of proteins. These three diamino acids are coded by codons of the genetic material and belong therefore to the canonic amino acids.

Ornithine and 2,6-diaminopimelic acid are non-proteinaceous diamino acids.

In biochemistry, diamino acids are of particular interest. Diamino acids are used for the synthesis of specific peptide nucleic acids, such as daPNA. Artificial peptide nucleic acids are capable forming duplex structures with individual DNA- and RNA-strands and are, therefore, not only called DNA-analog but also they are also considered as candidates for the first genetic material on Earth.^[1] The corresponding diamino acids such as 2,3-diaminopropanoic acid were detected in the Murchison meteorite ^[2] and in a simulated comet.^[3]

References and notes

1. ^ Egholm M, Buchardt O, Christensen L, Behrens C, Freier SM, Driver DA, Berg RH, Kim SK, Norden B, Nielsen PW (1993). "PNA hybridizes to complementary oligonucleotides obeying the Watson-Crick hydrogen bonding rules". Nature 365 (6446): 566–568. doi:10.1038/365566a0. PMID 7692304. 
2. ^ Meierhenrich UJ, Munoz Caro GM, Bredehöft JH, Jessberger EK, Thiemann WHP (2004). "Identification of diamino acids in the Murchison meteorite". PNAS 101 (25): 9182–9186. doi:10.1073/pnas.0403043101. PMC 438950. PMID 15194825. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=438950. 
3. ^ Munoz Caro GM, Meierhenrich UJ, Schutte WA, Barbier B, Arcones Segovia A, Rosenbauer H, Thiemann W, Brack A, Greenberg JM (2002). "Amino acids from ultraviolet irradiation of interstellar ice analogues". Nature 416 (6879): 403–406. doi:10.1038/416403a. PMID 11919624. 

Further reading

• Uwe Meierhenrich, Amino acids and the asymmetry of life, Springer-Verlag, 2008, ISBN 978-3-540-76885-2