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-PHE(3-I)-OH BOC-PHE(3-I)-OH 273221-75-3 C14H18INO4
BOC-L-3,4,5-TRIFLUOROPHENYLALANINE BOC-L-3,4,5-TRIFLUOROPHENYLALANINE 205445-54-1 C14H16F3NO4
BOC-(R)-3-AMINO-4-(4-PYRIDYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(4-PYRIDYL)-BUTYRIC ACID 269396-68-1 C14H20N2O4
Calcium 3-methyl-2-oxovalerate Calcium 3-methyl-2-oxovalerate 66872-75-1 C6H12CaO3
GRGDNP GRGDNP 114681-65-1 C23H38N10O10
CHLOROAC-D-PHE-OH CHLOROAC-D-PHE-OH 137503-97-0 C11H12ClNO3
FMOC-TIC-OH FMOC-TIC-OH 136030-33-6 C25H21NO4
N,N-Bis(2-hydroxyethyl)ethylenediamine N,N-Bis(2-hydroxyethyl)ethylenediamine 3197-06-6 C6H16N2O2
(R)-3-AMINO-4-(4-NITROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-NITROPHENYL)BUTANOIC ACID HYDROCHLORIDE 331763-78-1 C10H13ClN2O4
(S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE 110529-22-1 C18H21NO
BOC-DAP(BOC)-OH DCHA BOC-DAP(BOC)-OH DCHA 201472-68-6 C25H47N3O6
6-DIAZO-5-OXO-L-NORLEUCINE 6-DIAZO-5-OXO-L-NORLEUCINE 157-03-9 C6H9N3O3
FMOC-(S)-3-AMINO-3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 507472-20-0 C25H20F3NO4
3-[[(1,1-Dimethylethoxy)carbonyl]amino]-D-alanine methyl ester 3-[[(1,1-Dimethylethoxy)carbonyl]amino]-D-alanine methyl ester 363191-25-7 C9H18N2O4
BOC-(S)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID BOC-(S)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID 500770-74-1 C14H18ClNO4
FMOC-(R)-3-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID 511272-37-0 C24H19Cl2NO4
FMOC-(R)-3-AMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID 511272-31-4 C25H23NO5
(3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID (3S)-2-CARBOBENZOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID 79261-58-8 C18H17NO4
Glycine lauryl ester hydrochloride Glycine lauryl ester hydrochloride 16194-11-9 C14H30ClNO2
2-hydroxy-3-phenyl-L-alanine 2-hydroxy-3-phenyl-L-alanine 7423-92-9 C9H11NO3
ethyl L-isoleucinate hydrochloride ethyl L-isoleucinate hydrochloride 56782-52-6 C8H18ClNO2
Z-GLN-ONP Z-GLN-ONP 7763-16-8 C19H19N3O7
4-(BUTYLAMINO)BENZOIC ACID 4-(BUTYLAMINO)BENZOIC ACID 4740-24-3 C11H15NO2
BOC-L-BETA-HOMOASPARAGINE BOC-L-BETA-HOMOASPARAGINE 336182-03-7 C10H18N2O5
H-L-MEALA-OME HCL H-L-MEALA-OME HCL 35023-55-3 C5H11NO2
(R)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID HCL (R)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID HCL 331763-55-4 C10H13Cl2NO2
Z-PHE-PNA Z-PHE-PNA 19647-71-3 C23H21N3O5
FMOC-(S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID 501015-29-8 C25H23NO5
H-ASP(OBZL)-OTBU HCL H-ASP(OBZL)-OTBU HCL 94347-11-2 C15H21NO4
GAMMA-METHYL-L-LEUCINE GAMMA-METHYL-L-LEUCINE 57224-50-7 C7H15NO2
S-[2-(4-PYRIDYL)ETHYL]-L-CYSTEINE S-[2-(4-PYRIDYL)ETHYL]-L-CYSTEINE 28809-04-3 C10H14N2O2S
N-CARBAMYL-L-GLUTAMIC ACID N-CARBAMYL-L-GLUTAMIC ACID 1188-38-1 C6H10N2O5
D,L-3-CHLOROALANINE METHYL ESTER HYDROCHLORIDE D,L-3-CHLOROALANINE METHYL ESTER HYDROCHLORIDE 33646-31-0 C4H9Cl2NO2
FMOC-ASN(AC3ACNH-BETA-GLC)-OH FMOC-ASN(AC3ACNH-BETA-GLC)-OH 131287-39-3 C33H37N3O13
FMOC-(R)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID 788149-96-2 C25H22BrNO4
BOC-LYS(FOR)-OH BOC-LYS(FOR)-OH 2483-47-8 C12H22N2O5
FMOC-D-DAP-OH HCL FMOC-D-DAP-OH HCL 251317-00-7 C18H18N2O4
Z-PHE-ALA-OH Z-PHE-ALA-OH 21881-18-5 C20H22N2O5
4-AMINOCINNAMIC ACID HYDROCHLORIDE 4-AMINOCINNAMIC ACID HYDROCHLORIDE 54057-95-3 C9H10ClNO2
L-TERT-LEUCINE METHYLAMIDE L-TERT-LEUCINE METHYLAMIDE 89226-12-0 C7H16N2O
BOC-D-DAB(Z)-OH DCHA BOC-D-DAB(Z)-OH DCHA 101854-42-6 C29H47N3O6
POLY-L-ORNITHINE HYDROBROMIDE POLY-L-ORNITHINE HYDROBROMIDE 27378-49-0 C15H33Br3N6O3X2
FMOC-3,4-DEHYDRO-PRO-OH FMOC-3,4-DEHYDRO-PRO-OH 135837-63-7 C20H17NO4
H-MEILE-OH H-MEILE-OH 4125-98-8 C7H15NO2
(S)-2',6'-Dimethyltyrosine hydrochloride (S)-2',6'-Dimethyltyrosine hydrochloride 126312-63-8 C11H16ClNO3
DL-GLYCERIC ACID HEMICALCIUM SALT HYDRATE DL-GLYCERIC ACID HEMICALCIUM SALT HYDRATE 67525-74-0 C6H10CaO8
FMOC-D-LYS(BIOTIN)-OH FMOC-D-LYS(BIOTIN)-OH 110990-09-5 C31H38N4O6S
FMOC-ALA-OSU FMOC-ALA-OSU 73724-40-0 C22H20N2O6
CHLOROACETYL-DL-NORLEUCINE CHLOROACETYL-DL-NORLEUCINE 67206-26-2 C8H14ClNO3
BOC-CYS(ME)-OH BOC-CYS(ME)-OH 16947-80-1 C9H17NO4S
DL-4-CHLOROPHENYLALANINOL DL-4-CHLOROPHENYLALANINOL 35373-63-8 C9H12ClNO
AC-TRP-OME AC-TRP-OME 2824-57-9 C14H16N2O3
DL-NORMETANEPHRINE HYDROCHLORIDE DL-NORMETANEPHRINE HYDROCHLORIDE 1011-74-1 C9H14ClNO3
H-DL-ASP(OME)-OME HCL H-DL-ASP(OME)-OME HCL 14358-33-9 C6H12ClNO4
2-FLUORO-D-PHENYLALANINE 2-FLUORO-D-PHENYLALANINE 122839-51-4 C9H11ClFNO2
H-GLY-NHME HCL H-GLY-NHME HCL 49755-94-4 C3H9ClN2O
HIPPURYL-HIS-LEU HIPPURYL-HIS-LEU 31373-65-6 C21H27N5O5
H-GLY-HYP-OH H-GLY-HYP-OH 24587-32-4 C7H12N2O4
Fmoc-3-[[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-L-alanine Fmoc-3-[[1-(4,4-Dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-L-alanine 607366-20-1 C31H36N2O6
3-NITRO-D-TYROSINE 3-NITRO-D-TYROSINE 32988-39-9 C9H10N2O5
BOC-D-ORN(FMOC)-OH BOC-D-ORN(FMOC)-OH 163336-15-0 C25H30N2O6
N-BOC-L-ASPARAGINOL N-BOC-L-ASPARAGINOL 30044-67-8 C9H18N2O4
BOC-L-2-(5-BROMOTHIENYL)ALANINE BOC-L-2-(5-BROMOTHIENYL)ALANINE 190319-95-0 C12H16BrNO4S
BOC-(R)-3-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID 500788-90-9 C14H17Cl2NO4
FMOC-(R)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID 507472-28-8 C25H23NO4
FMOC-L-3-NITROPHENYLALANINE FMOC-L-3-NITROPHENYLALANINE 374791-01-2 C24H20N2O6
N-FORMYL-D-PHENYLALANINE N-FORMYL-D-PHENYLALANINE 59366-89-1 C10H11NO3
N-(1-NAPHTHALENESULFONYL)-L-PHENYLALANINE N-(1-NAPHTHALENESULFONYL)-L-PHENYLALANINE 90291-46-6 C19H17NO4S
3-Cyclopentane-L-alanine 3-Cyclopentane-L-alanine 99295-82-6 C8H15NO2
N-BOC-2-AMINO-2-METHYL-1-PROPANOL  97 N-BOC-2-AMINO-2-METHYL-1-PROPANOL 97 102520-97-8 C9H19NO3
(R)-(-)-2-BENZYLAMINO-1-PHENYLETHANOL (R)-(-)-2-BENZYLAMINO-1-PHENYLETHANOL 107171-75-5 C15H17NO
5,5,5-TRIFLUORO-DL-LEUCINE 5,5,5-TRIFLUORO-DL-LEUCINE 372-22-5 C6H10F3NO2
DL-2,6-DIFLUOROPHENYLALANINE DL-2,6-DIFLUOROPHENYLALANINE 32133-39-4 C9H9F2NO2
4-(TRIFLUOROMETHOXY)-DL-PHENYLGLYCINE 4-(TRIFLUOROMETHOXY)-DL-PHENYLGLYCINE 261952-24-3 C9H8F3NO3
Boc-6-AMinocaproic acid Boc-6-AMinocaproic acid 6404-29-1 C11H21NO4
AG 1295 AG 1295 71897-07-9 C16H14N2
BOC-DL-VALINE BOC-DL-VALINE 54895-12-4 C10H19NO4
FMOC-3-AMINOBENZOIC ACID FMOC-3-AMINOBENZOIC ACID 185116-42-1 C22H17NO4
N-ACETYL-5-BENZYLOXY-DL-TRYPTOPHAN N-ACETYL-5-BENZYLOXY-DL-TRYPTOPHAN 55443-80-6 C20H20N2O4
H-D-TRP(BOC)-OH H-D-TRP(BOC)-OH 201290-11-1 C16H20N2O4
DABSYL-L-VALINE DABSYL-L-VALINE 89131-11-3 C19H24N4O4S
Z-TLE-OH DCHA Z-TLE-OH DCHA 62965-37-1 C14H19NO4.C12H23N
H-GLU(OTBU)-NH2 HCL H-GLU(OTBU)-NH2 HCL 108607-02-9 C9H19ClN2O3
AC-PHE-OET AC-PHE-OET 2361-96-8 C13H17NO3
S-ETHYL-L-CYSTEINE S-ETHYL-L-CYSTEINE 2629-59-6 C5H11NO2S
METHYL 3,5-DIIODO-L-TYROSINATE METHYL 3,5-DIIODO-L-TYROSINATE 76318-50-8 C10H11I2NO3
2-AMINO-3-M-TOLYL-PROPIONIC ACID 2-AMINO-3-M-TOLYL-PROPIONIC ACID 5472-70-8 C10H13NO2
ALPHA-BOC-GAMMA-Z-(DL)-DIAMINOBUTYRIC ACID ALPHA-BOC-GAMMA-Z-(DL)-DIAMINOBUTYRIC ACID 16947-89-0 C29H47N3O6
AG 99 AG 99 122520-85-8 C10H8N2O3
L-THYRONINE L-THYRONINE 1596-67-4 C15H15NO4
BOC-(R)-3-AMINO-4-(3-FLUORO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3-FLUORO-PHENYL)-BUTYRIC ACID 331763-66-7 C15H20FNO4
(S)-3-AMINO-4-(3-THIENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-THIENYL)BUTANOIC ACID HYDROCHLORIDE 270262-99-2 C8H11NO2S
N-ALPHA-BENZOYL-L-ARGININAMIDE HYDROCHLORIDE N-ALPHA-BENZOYL-L-ARGININAMIDE HYDROCHLORIDE 4299-03-0 C13H20ClN5O2
Boc-D-Cyclopentylglycine Boc-D-Cyclopentylglycine 156881-63-9 C12H21NO4
BOC-GLY-PRO-OH BOC-GLY-PRO-OH 14296-92-5 C12H20N2O5
FMOC-(S)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID 270596-40-2 C25H22ClNO4
N-Fmoc-D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid N-Fmoc-D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 130309-33-0 C25H21NO4
D(+)-HISTIDINOL DIHYDROCHLORIDE D(+)-HISTIDINOL DIHYDROCHLORIDE 75614-84-5 C6H13Cl2N3O
Fmoc-beta-(S)-4-methoxyphenylalanine Fmoc-beta-(S)-4-methoxyphenylalanine 501015-30-1 C25H23NO5
D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI) D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI) 86123-95-7 C9H17NO5
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