Natural amino acids and derivatives

The amino acids are basic composites of protein, being the carboxylates containing amino groups in the molecules. There are over 200 kinds of naturally existing amino acids. But the number of amino acids constituting the animal's body and its protein product is only 20.

Structure and classification of amino acids
The structure of amino acid: amino acids obtained from protein hydrolysis are mostly α- amino acid with the α-carbon atom close to the carboxyl group bound with a amino group (-NH2 in), a carboxyl group (-COOH), a hydrogen atom and a side chain group. The side chain can be denoted as letter R, different R leads to different amino acids; the basic structure of the amino acid formula is as follows:
amino acid
Figure 1: the basic formula of amino acid.

Classification of amino acids according to the polarity of the R, amino acids can be classified into non-polar R group amino acids, uncharged polar R groups of amino acid and positively charged amino acids and negatively charged R-group amino acid. The first category includes alanine, leucine, isoleucine, valine, proline, phenylalanine, and methionine; the second category include glycine, serine, threonine, cysteine and casein acid; the third category include lysine, arginine, and threonine; fourth category include aspartic acid and glutamic acid.

In livestock production, according to different classification methods, amino acids can be divided into essential amino acids and non-essential amino acids, limiting amino acids and non-limiting amino acids.

Isomer: except the glycine (for which, the R group is a hydrogen atom), the alpha-carbons of all the rest amino acids [alpha] are asymmetric carbon atoms, thus having stereoisomers and therefore being optically active. According to the configuration of the α-carbon atom, amino acids can be divided into L-type and D-type. Amino acids originating from the proteolysis of animals and plants are all L-type. Amino acids produced by chemical synthesis and fermentation contain L-amino acids, D-amino acids and DL-amino acids of the mixture of equal amount of L and D type. Animal enzyme system can only directly use the L-amino acid for the protein synthesis of tissues. In addition to methionine, D-amino acids and DL-amino acids have very low utilization efficiency and can even not be exploited by animals.

General properties of amino acids
Physical properties natural amino acid appears as a colorless crystalline material with relatively high melting point, usually being above 200 ℃. It is usually soluble in water, insoluble in non-polar organic solvents. However, tyrosine and cystine are insoluble in water; proline and carboxylic proline can be dissolved in ethanol and ether. All kinds of amino acids are soluble in acid and alkali solution.
The acidity and alkalinity of amino acid amino acids are amphoteric electrolytes, being able to form salts with an acid or a base. The carboxyl group and amino group in the same molecule may also generate internal salts. In solution, amino acid is majorly in ionic form. If we adjust the pH of a certain amino acid solution to become nonconductive that the ions neither move towards cathode nor to anode, the pH of the solution in this case is referred as the isoelectric points of this amino acid, etc.

Chemical reactions related to the determination of amino acids
(1) The reaction with nitrous acid; amino acids can interact with nitrate to generate hydroxy acid and water, and quantitative release nitrogen.
(2) The reaction with 2, 4-nitro fluoro-benzene; upon near neutral or slightly alkaline conditions at room temperature, an amino group inside an amino acids molecule can react with 2, 4-nitro fluoro-benzene to generate the 2,4-nitro fluoro-benzene derivatives of amino acids, i.e., yellow DNP- amino acids.
(3) Reaction with dimethylamino-naphthalene sulfonyl chloride (DNS-CL); the fluorescent reagent DNS-CL can bind with the amino group of amino acids to form fluorescent DNS amino acid into the DNS. Lysine, histidine, aspartic acid, tyrosine and other amino acids can form pair DNS- amino acid derivatives of stable properties.
(4) The reaction with ninhydrin; α-amino acid can be oxidized and decomposed by ninhydrin to aldehyde, ammonia and CO2 while ninhydrin will be restored. The released ammonia can have condensation reaction with another molecule of ninhydrin and one molecule of ninhydrin reduction product to become blue-violet compound.

Separation and Determination of amino acids; amino acids are mostly bound amino acids; the first step of separating amino acids is using acid or base to hydrolyze protein, preparing the mixture of amino acids, then further perform partition chromatography and ion exchange chromatography for further separation and determination of amino acids.

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Structure Chemical Name CAS MF
H-ILE-NH2 HCL H-ILE-NH2 HCL 10466-56-5 C6H15ClN2O
H-PRO-OTBU H-PRO-OTBU 2812-46-6 C9H17NO2
H-PHE-NH2 H-PHE-NH2 5241-58-7 C9H12N2O
H-ASP(OET)-OET HCL H-ASP(OET)-OET HCL 16115-68-7 C8H16ClNO4
H-HIS(TRT)-OH H-HIS(TRT)-OH 35146-32-8 C25H23N3O2
H-L-CYS(TRT)-NH2 HCL H-L-CYS(TRT)-NH2 HCL 166737-85-5 C22H22N2OS
H-D-ASP(OBZL)-OH H-D-ASP(OBZL)-OH 13188-89-1 C11H13NO4
H-PRO-NME2 H-PRO-NME2 29802-22-0 C7H14N2O
N-FORMYL-L-METHIONINE N-FORMYL-L-METHIONINE 4289-98-9 C6H11NO3S
H-PHE-OBZL P-TOSYLATE H-PHE-OBZL P-TOSYLATE 88224-00-4 C12H15NO2.C7H8O3S
Biocytin Biocytin 576-19-2 C16H28N4O4S
D-ASPARTIC ACID(OBZL)-OBZL P-TOSYLATE D-ASPARTIC ACID(OBZL)-OBZL P-TOSYLATE 4079-64-5 C25H27NO7S
H-TYR-NH2 HCL H-TYR-NH2 HCL 4985-46-0 C9H12N2O2
H-GLU(OBZL)-OTBU HCL H-GLU(OBZL)-OTBU HCL 105590-97-4 C16H24ClNO4
H-D-PRO-NH2 HCL H-D-PRO-NH2 HCL 50894-62-7 C5H11ClN2O
N-EPSILON-ACETYL-L-LYSINE N-EPSILON-ACETYL-L-LYSINE 692-04-6 C8H16N2O3
H-D-GLU(OTBU)-OH H-D-GLU(OTBU)-OH 45125-00-6 C9H17NO4
H-GLU(OALL)-OALL P-TOSYLATE H-GLU(OALL)-OALL P-TOSYLATE 20845-16-3 C18H25NO7S
H-GLU(OBZL)-OBZL HCL H-GLU(OBZL)-OBZL HCL 4561-10-8 C19H22ClNO4
H-VAL-ALA-OH H-VAL-ALA-OH 27493-61-4 C8H16N2O3
H-D-PRO-OTBU H-D-PRO-OTBU 90071-62-8 C9H17NO2
H-VAL-TRP-OH H-VAL-TRP-OH 24587-37-9 C16H21N3O3
H-PRO-HYP-OH H-PRO-HYP-OH 18684-24-7 C10H16N2O4
GLYCYLGLYCINE METHYL ESTER HYDROCHLORIDE GLYCYLGLYCINE METHYL ESTER HYDROCHLORIDE 2776-60-5 C5H11ClN2O3
H-ASP(OBZL)-OBZL HCL H-ASP(OBZL)-OBZL HCL 6327-59-9 C18H20ClNO4
H-D-LEU-NH2 HCL H-D-LEU-NH2 HCL 80970-09-8 C6H15ClN2O
AC-ASP(OTBU)-OH AC-ASP(OTBU)-OH 117833-18-8 C10H17NO5
AC-DL-PRO-OH AC-DL-PRO-OH 1074-79-9 C7H11NO3
H-D-LYS(BOC)-OME HCL H-D-LYS(BOC)-OME HCL 66494-53-9 C12H25ClN2O4
H-TRP(BOC)-OH H-TRP(BOC)-OH 146645-63-8 C16H20N2O4
H-PRO-GLY-OH H-PRO-GLY-OH 2578-57-6 C7H12N2O3
H-DL-LEU-OME HCL H-DL-LEU-OME HCL 6322-53-8 C7H16ClNO2
H-GLY-HYP-OH H-GLY-HYP-OH 24587-32-4 C7H12N2O4
H-DL-LEU-NH2 HCL H-DL-LEU-NH2 HCL 10466-60-1 C6H15ClN2O
ETHYL 2-AMINO-3-HYDROXYPROPANOATE HYDROCHLORIDE ETHYL 2-AMINO-3-HYDROXYPROPANOATE HYDROCHLORIDE 3940-27-0 C5H12ClNO3
H-D-TRP(BOC)-OH H-D-TRP(BOC)-OH 201290-11-1 C16H20N2O4
H-GLU(OTBU)-NH2 HCL H-GLU(OTBU)-NH2 HCL 108607-02-9 C9H19ClN2O3
H-ASP(OBZL)-OTBU HCL H-ASP(OBZL)-OTBU HCL 94347-11-2 C15H21NO4
AC-TRP-OME AC-TRP-OME 2824-57-9 C14H16N2O3
H-DL-ASP(OME)-OME HCL H-DL-ASP(OME)-OME HCL 14358-33-9 C6H12ClNO4
H-HIS-NH2 2HCL H-HIS-NH2 2HCL 71666-95-0 C6H12Cl2N4O
H-D-SER(TBU)-OTBU HCL H-D-SER(TBU)-OTBU HCL 179559-35-4 C11H24ClNO3
H-D-LEU-GLY-OH H-D-LEU-GLY-OH 997-05-7 C8H16N2O3
D-ASPARTIC ACID-BETA-METHYL ESTER D-ASPARTIC ACID-BETA-METHYL ESTER 21394-81-0 C5H9NO4
AC-LYS (BOC)-OH AC-LYS (BOC)-OH 23500-04-1 C13H24N2O5
O-ACETYL-L-SERINE O-ACETYL-L-SERINE 5147-00-2 C5H9NO4
H-GLY-MET-OH H-GLY-MET-OH 554-94-9 C7H14N2O3S
H-D-VAL-NH2 HCL H-D-VAL-NH2 HCL 133170-58-8 C5H13ClN2O
H-D-THR(TBU)-OH H-D-THR(TBU)-OH 201274-81-9 C8H17NO3
H-D-GLU(OME)-OH H-D-GLU(OME)-OH 6461-04-7 C6H11NO4
DDE-LYS(FMOC)-OH DDE-LYS(FMOC)-OH 156648-40-7 C31H36N2O6
H-PHE-NHNH2 H-PHE-NHNH2 52386-52-4 C9H13N3O
AC-TYR(AC)-OH AC-TYR(AC)-OH 17355-23-6 C13H15NO5
O-ACETYL-L-TYROSINE O-ACETYL-L-TYROSINE 6636-22-2 C11H13NO4
H-Ser-OtBu · HCl H-Ser-OtBu · HCl 106402-41-9 C7H15NO3.ClH
H-D-CYS(ACM)-OH HCL H-D-CYS(ACM)-OH HCL 200352-41-6 C6H13ClN2O3S
L-LEUCINE ALLYL ESTER P-TOLUENESULFONATE SALT L-LEUCINE ALLYL ESTER P-TOLUENESULFONATE SALT 88224-03-7 C16H25NO5S
D-Alanine Isopropyl Ester HCl D-Alanine Isopropyl Ester HCl 39613-92-8 C6H14ClNO2
AC-CYS(TRT)-OH AC-CYS(TRT)-OH 27486-87-9 C24H23NO3S
H-CYS(ACM)-NH2 HCL H-CYS(ACM)-NH2 HCL 88530-32-9 C6H13N3O2S
H-D-GLU(OBZL)-OBZL HCL H-D-GLU(OBZL)-OBZL HCL 146844-02-2 C19H22ClNO4
N-[2-(DIETHYLAMINO)ETHYL]STEARAMIDE N-[2-(DIETHYLAMINO)ETHYL]STEARAMIDE 16889-14-8 C24H50N2O
H-PHE-LEU-OH H-PHE-LEU-OH 3303-55-7 C15H22N2O3
H-CYS(DPM)-OH H-CYS(DPM)-OH 5191-80-0 C16H17NO2S
H-D-Asp(OtBu)-OtBu · HCl H-D-Asp(OtBu)-OtBu · HCl 135904-71-1 C12H23NO4.HCl
H-VAL-PNA H-VAL-PNA 52084-13-6 C11H15N3O3
H-PHE-ALA-OH H-PHE-ALA-OH 3918-87-4 C12H16N2O3
TOS-PRO-OH TOS-PRO-OH 51077-01-1 C12H15NO4S
S-(acetamidomethyl)-L-cysteine S-(acetamidomethyl)-L-cysteine 19647-70-2 C6H12N2O3S
H-LYS(ALLOC)-OH H-LYS(ALLOC)-OH 6298-03-9 C10H18N2O4
H-PRO-NHET HCL H-PRO-NHET HCL 58107-62-3 C7H15ClN2O
H-ALA-ALA-OME HCL H-ALA-ALA-OME HCL 41036-19-5 C7H15ClN2O3
L-BAME L-BAME 1784-04-9 C15H22N4O6
H-Glu(OtBu)-OBzl.HCl H-Glu(OtBu)-OBzl.HCl 98102-32-0 C16H24ClNO4
H-D-THR(TBU)-OME HCL H-D-THR(TBU)-OME HCL 115141-43-0 C9H20ClNO3
AC-LYS(Z)-OH AC-LYS(Z)-OH 6367-08-4 C16H22N2O5
H-Arg(Pbf)-OH H-Arg(Pbf)-OH 200115-86-2 C19H30N4O5S
L-THREONINE BENZYL ESTER HYDROCHLORIDE L-THREONINE BENZYL ESTER HYDROCHLORIDE 33645-24-8 C11H16ClNO3
TOSYL-D-VALINE TOSYL-D-VALINE 68005-71-0 C12H17NO4S
H-D-LYS(Z)-OME HCL H-D-LYS(Z)-OME HCL 145586-17-0 C15H22N2O4
H-DL-MET-OME HCL H-DL-MET-OME HCL 16118-36-8 C6H14ClNO2S
AC-GLY-GLY-OH AC-GLY-GLY-OH 5687-48-9 C6H10N2O4
AC-TYR-OME H2O AC-TYR-OME H2O 2440-79-1 C12H15NO4
H-GLY-GLY-PHE-OH H-GLY-GLY-PHE-OH 6234-26-0 C13H17N3O4
AC-THR(TBU)-OH AC-THR(TBU)-OH 163277-80-3 C10H19NO4
H-D-GLU(OTBU)-OTBU HCL H-D-GLU(OTBU)-OTBU HCL 172793-31-6 C13H26ClNO4
TOS-ALA-OH TOS-ALA-OH 99076-56-9 C10H13NO4S
H-DL-ASP-OME H-DL-ASP-OME 65414-77-9 C5H9NO4
H-D-GLN(TRT)-OH H-D-GLN(TRT)-OH 200625-76-9 C24H24N2O3
D-Aspartic Acid diethyl ester hydrochloride D-Aspartic Acid diethyl ester hydrochloride 112018-26-5 C8H16ClNO4
H-Tyr(Tos)-OH H-Tyr(Tos)-OH 159505-46-1 C16H17NO5S
H-His(Trt)-OMe · HCl H-His(Trt)-OMe · HCl 32946-56-8 C26H25N3O2.ClH
O-Benzyl-DL-Serine O-Benzyl-DL-Serine 32520-12-0 C10H13NO3
H-D-Glutamic aicd diethyl ester hydrochloride H-D-Glutamic aicd diethyl ester hydrochloride
H-Glu(OMe)-OtBu H-Glu(OMe)-OtBu 34582-33-7 C10H20ClNO4
BENZOYL-D-PHE-OH BENZOYL-D-PHE-OH 37002-52-1 C16H15NO3
D-THREONINE BENZYL ESTER HYDROCHLORIDE D-THREONINE BENZYL ESTER HYDROCHLORIDE 75748-36-6 C11H16ClNO3
H-ALA-PRO-OME HCL H-ALA-PRO-OME HCL 71067-42-0 C9H17ClN2O3
H-D-LEU-LEU-OH H-D-LEU-LEU-OH 38689-31-5 C12H24N2O3
AC-SER(TBU)-OH AC-SER(TBU)-OH 77285-09-7 C9H17NO4
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