16. α –Amino acids - classification. Chemical properties of α -amino acids. Chemical aspects of amino acid metabolism – deamination of α -amino acids; ketogenic and glucogenic amino acids.
Topic 16 of 26 in the MU Plovdiv syllabus for Chemistry (Medicine, Year 1). The free AceMed note covers it in 8 sections, about 916 words (6 min of reading), with 19 flashcards.
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α-Amino acids - structure, nomenclature,
Stereochemistry.:
Essential amino acids.
Acid-base properties
Isoelectric point.
Chemical properties.
Esterification, acylation and interaction with formaldehyde and ninhydrin.
Amino acid analysis - diagnostic significance.
α-Amino acids - structure, nomenclature,
Amino acids:
Contain carboxylic acid group (-COOH) and amino group (-NH2).
Usually α- to the carboxylic acid (means they are attached to adjacent carbon atoms in the molecule).
Classified as α-, β-, γ-, etc. based on relative positions of functional groups.
α-Amino acids:
Most important biologically.
Amino and carboxyl groups are α- to each other.
Structures may have various functional groups.
Classification based on functional groups:
I. Neutral:
I.1. Non-polar R-groups.
I.2. Non-charged polar (non-ionized) R-groups.
II. Acidic:
Contain acidic functional groups.
III. Basic:
Contain basic functional groups.
Stereochemistry.:
Amino acids are chiral molecules.
Except for glycine, which has two identical substituents on the α-carbon, α-amino acids have four different substituents, making them chiral.
The α-carbon is the chiral center.
Naturally occurring amino acids predominantly exist in the L-configuration, where the amino group is on the left side when the carboxyl group is at the top.
The D-configuration also exists but is less common in naturally occurring proteins.
The stereochemistry of amino acids is crucial for the folding and function of proteins.
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