FComEx: D-Lysine (PC000878)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:11 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000878

FoodDB Record

FDB023163

Chemical Information

Name

D-Lysine

Description

Lysine and its bioactive form L-lysine, abbreviated Lys or L, is an essential amino acid. Normal requirements for adults are between 8 g per day or 12 mg/kg. Children and infants need more: 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize these levels and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture and has helped to reduce the number and occurrence of cold sores in clinical studies. Beneficial clinical effects occurred with lysine doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes as excess arginine antagonizes lysine. Lysine also may be a useful adjunct in the treatment of osteoporosis because it reduces calcium losses in urine. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine is high in foods such as wheat germ, cottage cheese, chicken, wild game and pork. Less lysine is found in apple, apricot, bananas, avocados, guava, lime, brazil nuts, cashews, mung bean, fava bean and black bean as well as other seeds, nuts and fruits.

CAS Number

923-27-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(R)-2,6-Diaminohexanoate	Generator
(R)-2,6-Diaminohexanoic acid	ChEBI
D-2,6-Diaminohexanoate	hmdb
D-2,6-Diaminohexanoic acid	hmdb
D-Lysin	ChEBI

Chemical Formula

C6H14N2O2

IUPAC name

(2R)-2,6-diaminohexanoic acid

InChI Identifier

InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1

InChI Key

KDXKERNSBIXSRK-RXMQYKEDSA-N

Isomeric SMILES

NCCCC[C@@H](N)C(O)=O

Average Molecular Weight

146.19

Monoisotopic Molecular Weight

146.105527699

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-alpha-amino acids

Alternative Parents