Amino Acids and Derivatives

Amino acids and their derivatives belong to a compound containing both amino group and carboxyl group. They are presented in both the form of free-state and bound-state in vivo. Free amino acids are distributed in all kinds of animal cells and body fluids with the bound amino acids being the mainly basic components of proteins and peptides.

Natural amino acids act as colorless crystalline materials with relatively high melting points being mostly above 200 ℃. They are usually soluble in water but insoluble in non-polar organic solvents. However, tyrosine and cystine are insoluble in water; proline and hydroxyl proline are soluble in ethanol and ether. All amino acids are soluble in strong acid and alkali solution.

According to the polar characterization of the R group of the side chain of the α-amino acid; those 20 common amino acids that constitute protein can be divided into four groups:
① Amino acids with R group being non-polar; There are 8 kinds in total, wherein five kinds have aliphatic side chains, namely alanine, leucine, isoleucine, valine and proline; two kinds are aromatic amino acids, phenylalanine and tryptophan; one kind belongs to sulfur-containing amino acid, namely methionine; amino acids belonging to this group have lower water solubility than polar R-group amino acid; proline is generally different with α-amino acid, it is formed through the substitution of one hydrogen atom of the amino acid with the side chains of the α- amino acid, belonging actually to imino acid.
② Amino acids with polar but non-charged R group; There are seven kinds in total, namely serine, threonine and tyrosine with R group having hydroxy group; cysteine with R group having a mercapto group of cysteine; glutamine and asparagine with R-group containing amide group, another amino acid is glycine ; glycine molecule has no R group, but having certain polarity, and thus being classified into this group; the side chains in this group of amino acid contain unassociated polar groups and can form hydrogen bonds with water, and is easily soluble in water.
③Amino acids with R group being positively charged amino acids. There are three kinds in total, namely, lysine, arginine, and histidine; they carry positive charge at pH7.0 and are also known as alkaline amino acids.
④Amino acids with R group being negatively charged. There are two kinds in total, namely glutamate and aspartate; at pH7.0, the molecules are negatively charged, also known as acidic amino acids. The formula, abbreviations symbols and related constants of 20 kinds of amino acid structures can be seen from the table. In addition to the 20 common amino acids mentioned above, there are also diiodotyrosine, thyroxine, hydroxyproline and hydroxylysine existing in certain proteins. In addition to amino acids involved in protein composition, it has been also found of more than 200 kinds of other kinds amino acids in a variety of tissues and cells; these amino acids are mostly derivatives of those α- amino acid composition of proteins.

However, there are some β-, γ- or δ- amino acids and some amino acids belong to D-type amino acids such as [beta]-alanine, [gamma]-aminobutyric acid and the phenylalanine contained in the antibiotics gramicidin-S, the D-alanine and D-glutamate contained in Gram-positive bacteria cell wall. Some non-protein amino acids can act as metabolically important precursors or intermediates, wherein β-alanine is the precursors of vitamin pantothenic acid; ornithine, and citrulline are the precursors in the synthesis of arginine; [gamma]-aminobutyric acid is the chemical neurotransmitter. Plants contain a large amount of non-protein amino acids, belonging to plant secondary substances, such as theanine, canavanine, djenkolic acid, β- Cyanoalanine and so on.

In addition to 20 kinds of amino acids found in the body and animal protein products, it has been found of nearly 200 kinds of other kinds of amino acids in nature. Most of them have been discovered in the plant kingdom and have complex molecular structures with no relation with the protein metabolism. There have been less that have been seen in the animal kingdom with some of them being originated from the chemical modification of certain incorporated amino acids in the specific proteins, for example, the proline and lysine contained in collagen protein are often partially subject to re-hydroxylation of hydroxyproline and hydroxylysine; Another example is that there are often a small amount of lysine and histidine contained in actin and myosin protein containing hypermethylated εN methyl-lysine and 3N-histidine; it has been also found in the histone protein that the ∈ amino group contained in lysine is acetylated and the OH group in the serine is phosphorylated; thyroglobulin contains iodinated tyrosine and thyronine iodide; The heavy chain of τ myosin and the N-terminal of certain proteins contain pyroglutamate formed by glutamine; there also exists the cystine constituting of two cysteine molecules in the general protein.

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Structure Chemical Name CAS MF
BOC-ARG-OH BOC-ARG-OH 13726-76-6 C11H22N4O4
GLYCYLGLYCINE METHYL ESTER HYDROCHLORIDE GLYCYLGLYCINE METHYL ESTER HYDROCHLORIDE 2776-60-5 C5H11ClN2O3
N6-Trifluoroacetyl-L-lysyl-L-proline N6-Trifluoroacetyl-L-lysyl-L-proline 103300-89-6 C13H20F3N3O4
Boc-N-beta-Trityl-L-asparagine Boc-N-beta-Trityl-L-asparagine 132388-68-2 C28H30N2O5
(R)-3-AMINO-4-(3-BENZOTHIENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(3-BENZOTHIENYL)BUTANOIC ACID HYDROCHLORIDE 269398-95-0 C12H13NO2S
N-Boc-cis-4-Fmoc-Amino-L-proline N-Boc-cis-4-Fmoc-Amino-L-proline 174148-03-9 C25H28N2O6
Z-TRANS-4-HYDROXY-L-PROLINOL Z-TRANS-4-HYDROXY-L-PROLINOL 95687-41-5 C13H17NO4
3-(2-Quinolyl)-DL-alanine 3-(2-Quinolyl)-DL-alanine 123761-12-6 C12H12N2O2
FMOC-LYS(BOC)(ME)-OH FMOC-LYS(BOC)(ME)-OH 951695-85-5 C27H34N2O6
BOC-(S)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID 270065-86-6 C16H20N2O4
FMOC-CYS(MMT)-OH FMOC-CYS(MMT)-OH 177582-21-7 C38H33NO5S
BOC-D-TYR(ME)-OH BOC-D-TYR(ME)-OH 68856-96-2 C15H21NO5
BOC-(R)-3-AMINO-4-(3,4-DIFLUORO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3,4-DIFLUORO-PHENYL)-BUTYRIC ACID 269396-59-0 C15H19F2NO4
FMOC-(S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID 479064-89-6 C24H20FNO4
DL-O-METHYLSERINE DL-O-METHYLSERINE 19794-53-7 C4H9NO3
N-FORMYL-L-TYROSINE N-FORMYL-L-TYROSINE 13200-86-7 C10H11NO4
DL-2,4-DIAMINOBUTYRIC ACID DIHYDROCHLORIDE DL-2,4-DIAMINOBUTYRIC ACID DIHYDROCHLORIDE 65427-54-5 C4H12Cl2N2O2
(S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(2-FLUORO-PHENYL)-PROPIONIC ACID 151911-32-9 C9H10FNO2
PTH-TYROSINE PTH-TYROSINE 4332-95-0 C16H14N2O2S
N,N-DI-N-PROPYL-L-ALANINE N,N-DI-N-PROPYL-L-ALANINE 81854-56-0 C9H19NO2
GLYCYL-D-ASPARTIC ACID GLYCYL-D-ASPARTIC ACID 17343-03-2 C6H10N2O5
FMOC-D-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID FMOC-D-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID 268731-07-3 C27H22N2O4
PHENYLTHIOHYDANTOIN-THREONINE PHENYLTHIOHYDANTOIN-THREONINE 5789-21-9 C11H12N2O2S
3-Bromo-L-phenylalanine 3-Bromo-L-phenylalanine 82311-69-1 C9H10BrNO2
Boc-S-Benzyl-L-cysteine Boc-S-Benzyl-L-cysteine 5068-28-0 C15H21NO4S
FMOC-D-3,5-DIFLUOROPHE FMOC-D-3,5-DIFLUOROPHE 205526-25-6 C24H19F2NO4
1-BOC-D-PYROGLUTAMIC ACID ETHYL ESTER
1-BOC-D-PYROGLUTAMIC ACID ETHYL ESTER 144978-35-8 C12H19NO5
N-FORMYL-L-METHIONINE N-FORMYL-L-METHIONINE 4309-82-4 C6H11NO3S
1H-Pyrazole-4-carboxylicacid,5-amino-1-methyl-(9CI) 1H-Pyrazole-4-carboxylicacid,5-amino-1-methyl-(9CI) 4058-91-7 C5H7N3O2
H-THR(TBU)-OTBU H-THR(TBU)-OTBU 5854-78-4 C12H25NO3
N-BENZYLOXYCARBONYL-D-ALANINOL N-BENZYLOXYCARBONYL-D-ALANINOL 61425-27-2 C11H15NO3
FMOC-(S)-3-AMINO-4-(4-BROMO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(4-BROMO-PHENYL)-BUTYRIC ACID 270062-86-7 C25H22BrNO4
FMOC-(S)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 270065-75-3 C26H22F3NO4
L-Arginine acetate L-Arginine acetate 71173-62-1 C8H18N4O4
Z-ASN(TRT)-OH Z-ASN(TRT)-OH 132388-57-9 C31H28N2O5
DL-ALANINE BETA-NAPHTHYLAMIDE HYDROCHLORIDE DL-ALANINE BETA-NAPHTHYLAMIDE HYDROCHLORIDE 74144-49-3 C13H15ClN2O
DL-METHIONINE SULFOXIDE DL-METHIONINE SULFOXIDE 62697-73-8 C5H11NO3S
DL-2-METHYLGLUTAMIC ACID DL-2-METHYLGLUTAMIC ACID 71-90-9 C6H11NO4
(S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE (S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE 15295-77-9 C4H8BrNO2
FMOC-(R)-3-AMINO-4-(4-CYANO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(4-CYANO-PHENYL)-BUTYRIC ACID 269726-87-6 C26H22N2O4
(R)-N-Acetyl-2-naphthylalanine (R)-N-Acetyl-2-naphthylalanine 37440-01-0 C15H15NO3
H-PRO-HYP-OH H-PRO-HYP-OH 18684-24-7 C10H16N2O4
GLYCYL-DL-SERINE GLYCYL-DL-SERINE 687-38-7 C5H10N2O4
N'-Methyl-L-histidine methyl ester N'-Methyl-L-histidine methyl ester 57519-09-2 C8H13N3O2
N-CARBOBENZOXY-DL-NORLEUCINE N-CARBOBENZOXY-DL-NORLEUCINE 15027-13-1 C14H19NO4
H-MET-OTBU HCL H-MET-OTBU HCL 91183-71-0 C9H20ClNO2S
N-(2,4-DINITROPHENYL)-L-ALANINE N-(2,4-DINITROPHENYL)-L-ALANINE 1655-52-3 C9H9N3O6
N-(1-NAPHTHALENESULFONYL)-L-PHENYLALANYL CHLORIDE N-(1-NAPHTHALENESULFONYL)-L-PHENYLALANYL CHLORIDE 146864-62-2 C19H16ClNO3S
FMOC-D-ASP-OTBU FMOC-D-ASP-OTBU 134098-70-7 C23H25NO6
(R)-3-AMINO-5-HEXENOIC ACID HYDROCHLORIDE (R)-3-AMINO-5-HEXENOIC ACID HYDROCHLORIDE 82448-92-8 C6H11NO2
BOC-TRP(BOC)-OH BOC-TRP(BOC)-OH 144599-95-1 C21H28N2O6
DL-ALANYL-GLYCINE DL-ALANYL-GLYCINE 1188-01-8 C5H10N2O3
N-FORMYL-L-HISTIDINE N-FORMYL-L-HISTIDINE 15191-21-6 C7H9N3O3
FMOC-(2-INDA)GLY-OH FMOC-(2-INDA)GLY-OH 205526-39-2 C26H23NO4
FMOC-(R)-3-AMINO-4-(3,4-DICHLORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3,4-DICHLORO-PHENYL)-BUTYRIC ACID 269396-57-8 C25H21Cl2NO4
H-GLY-ASN-OH H-GLY-ASN-OH 1999-33-3 C6H11N3O4
5-BROMO-DL-TRYPTOPHAN 5-BROMO-DL-TRYPTOPHAN 6548-09-0 C11H11BrN2O2
FMOC-(R)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID 269398-89-2 C29H25NO4
(2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID (2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID 118758-48-8 C11H13NO2
Cbz-Gly-Gly Cbz-Gly-Gly 2566-19-0 C12H14N2O5
2-Methyl-L-serine 2-Methyl-L-serine 16820-18-1 C4H9NO3
DL-BETA-PHENYLSERINE THREO FORM DL-BETA-PHENYLSERINE THREO FORM 69-96-5 C9H11NO3
(R)-3-AMINO-4-(3,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(3,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 269396-55-6 C10H11Cl2NO2
H-ALA-PNA HCL H-ALA-PNA HCL 31796-55-1 C9H12ClN3O3
BOC-D-DAP(FMOC)-OH BOC-D-DAP(FMOC)-OH 131570-56-4 C23H26N2O6
BOC-L-CYCLOPROPYLALANINE-DCHA BOC-L-CYCLOPROPYLALANINE-DCHA 89483-07-8 C23H42N2O4
FMOC-L-4-THIAZOLYLALANINE FMOC-L-4-THIAZOLYLALANINE 205528-32-1 C21H18N2O4S
Zinc methionine sulfate Zinc methionine sulfate 56329-42-1 C5H11NO6S2Zn
DL-Aspartic acid hemimagnesium salt DL-Aspartic acid hemimagnesium salt 1187-91-3 C4H5MgNO4
FMOC-(S)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID 270063-49-5 C25H21Cl2NO4
[2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid 166108-71-0 C21H23NO6
N-BENZOYL-DL-METHIONINE N-BENZOYL-DL-METHIONINE 4703-38-2 C12H15NO3S
BOC-(R)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID 269726-80-9 C16H20N2O4
PHENYLTHIOHYDANTOIN-TRYPTOPHAN PHENYLTHIOHYDANTOIN-TRYPTOPHAN 5789-24-2 C18H15N3OS
FMOC-(S)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRIC ACID 270596-49-1 C25H22FNO4
BOC-3,4-DIMETHOXY-L-PHENYLALANINE BOC-3,4-DIMETHOXY-L-PHENYLALANINE 127095-97-0 C16H23NO6
(R)-3-AMINO-4-(2-METHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(2-METHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE 269398-79-0 C11H15NO2
(R)-(+)-alpha-Amino-gamma-butyrolactone hydrochloride (R)-(+)-alpha-Amino-gamma-butyrolactone hydrochloride 104347-13-9 C4H8ClNO2
H-VAL-TRP-OH H-VAL-TRP-OH 24587-37-9 C16H21N3O3
BOC-(S)-3-AMINO-4-(3-THIENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-THIENYL)-BUTYRIC ACID 270263-00-8 C13H19NO4S
6-HYDROXYDOPAMINE HYDROBROMIDE 6-HYDROXYDOPAMINE HYDROBROMIDE 636-00-0 C8H12BrNO3
NALPHA-(2,4-DINITROPHENYL)-L-ARGININE NALPHA-(2,4-DINITROPHENYL)-L-ARGININE 1602-42-2 C12H16N6O6
5-METHOXY-DL-TRYPTOPHAN 5-METHOXY-DL-TRYPTOPHAN 28052-84-8 C12H14N2O3
Boc-D-aspartic acid 4-cyslohexyl ester Boc-D-aspartic acid 4-cyslohexyl ester 112898-18-7 C15H25NO6
BOC-(R)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 269726-74-1 C16H20F3NO4
3-DIMETHYLAMINOBENZYL ALCOHOL 3-DIMETHYLAMINOBENZYL ALCOHOL 23501-93-1 C9H13NO
BOC-D-LEU-OH H2O BOC-D-LEU-OH H2O 200937-17-3 C11H23NO5
(S)-3-AMINO-4-(1-NAPHTHYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(1-NAPHTHYL)BUTANOIC ACID HYDROCHLORIDE 270063-00-8 C14H15NO2
BOC-(S)-3-AMINO-5-HEXYNOIC ACID BOC-(S)-3-AMINO-5-HEXYNOIC ACID 270596-47-9 C11H17NO4
AG 18 AG 18 118409-57-7 C10H6N2O2
(S)-3-AMINO-4-(3-METHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-METHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE 270062-92-5 C11H15NO2
DL-Ephedrine hydrochloride DL-Ephedrine hydrochloride 134-71-4 C10H16ClNO
N'-Fmoc-L-lysine N'-Fmoc-L-lysine 84624-28-2 C21H24N2O4
(R)-3-AMINO-4-(4-METHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-METHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE 177839-85-9 C11H15NO2
(2S,4R)-4-METHYLGLUTAMIC ACID (2S,4R)-4-METHYLGLUTAMIC ACID 31137-74-3 C6H11NO4
Nalpha-Fmoc-Ndelta-Boc-L-ornithine Nalpha-Fmoc-Ndelta-Boc-L-ornithine 109425-55-0 C25H30N2O6
3-Amino-L-tyrosine 3-Amino-L-tyrosine 300-34-5 C9H12N2O3
METHYL 4-AMINO-6-INDOLECARBOXYLATE METHYL 4-AMINO-6-INDOLECARBOXYLATE 121561-15-7 C10H10N2O2
N-Methyl-L-phenylalanine N-Methyl-L-phenylalanine 2566-30-5 C10H13NO2
L-ARGININE P-NITROANILIDE DIHYDROCHLORIDE L-ARGININE P-NITROANILIDE DIHYDROCHLORIDE 40127-11-5 C12H19ClN6O3
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