The α-carbon of every amino acid except glycine is a stereocenter. If its proton is removed and returned from the other side, as can happen while an amino acid is activated for coupling in synthesis, the residue changes configuration from L to D or back.
In a peptide, one residue in the wrong configuration gives a diastereomer: the same sequence and mass, a different three-dimensional shape. Diastereomers are found by chromatography or chiral analysis, not by mass spectrometry.
See also
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Cosmic Peptides. (2026, October 25). Racemization: glossary entry. Cosmic Peptides Research Library. Retrieved October 26, 2026, from https://cosmicpeptides.com/research/glossary/racemization
BibTeX
@misc{cosmicpeptides_research_glossary_racemization,
author = {{Cosmic Peptides}},
title = {Racemization: glossary entry},
howpublished = {Cosmic Peptides Research Library},
year = {2026},
month = oct,
url = {https://cosmicpeptides.com/research/glossary/racemization},
urldate = {2026-10-26},
note = {Last reviewed 2026-10-25}
} RIS
TY - ELEC AU - Cosmic Peptides TI - Racemization: glossary entry T2 - Cosmic Peptides Research Library PB - Cosmic Peptides PY - 2026 DA - 2026/10/25 UR - https://cosmicpeptides.com/research/glossary/racemization Y2 - 2026/10/26 LA - en ER -
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