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
3-FLUORO-D-PHENYLALANINE 3-FLUORO-D-PHENYLALANINE 2629-54-1 C9H10FNO2
KYNURENIC ACID KYNURENIC ACID 492-27-3 C10H7NO3
DL-LEUCYL-GLYCYL-GLYCINE DL-LEUCYL-GLYCYL-GLYCINE 4337-37-5 C10H19N3O4
N-Carbobenzyloxyglycine N-Carbobenzyloxyglycine 1138-80-3 C10H11NO4
D-Leucine methyl ester hydrochloride D-Leucine methyl ester hydrochloride 5845-53-4 C7H16ClNO2
Fmoc-3-chloro-D-phenylalanine Fmoc-3-chloro-D-phenylalanine 205526-23-4 C24H20ClNO4
(R)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID 131690-61-4 C9H10ClNO2
Fmoc-Met-OH Fmoc-Met-OH 112883-40-6 C20H21NO4S
H-D-DAP-OH HCL H-D-DAP-OH HCL 6018-56-0 C3H9ClN2O2
L(+)-2-Aminobutyric acid L(+)-2-Aminobutyric acid 1492-24-6 C4H9NO2
4-Fluorophenylglycine 4-Fluorophenylglycine 7292-73-1 C8H8FNO2
D-1-Naphthylalanine D-1-Naphthylalanine 78306-92-0 C13H13NO2
H-MEVAL-OH HCL H-MEVAL-OH HCL 2480-23-1 C6H13NO2
6-FLUORO-DL-TRYPTOPHAN 6-FLUORO-DL-TRYPTOPHAN 7730-20-3 C11H11FN2O2
Fmoc-3-chloro-L-phenylalanine Fmoc-3-chloro-L-phenylalanine 198560-44-0 C24H20ClNO4
Fmoc-D-phenylalanine Fmoc-D-phenylalanine 86123-10-6 C24H21NO4
N-Acetyl-DL-tryptophan N-Acetyl-DL-tryptophan 87-32-1 C13H14N2O3
BOC-L-3-THIENYLALANINE DCHA SALT BOC-L-3-THIENYLALANINE DCHA SALT 83825-42-7 C12H17NO4S
Boc-Arg(Tos)-OH Boc-Arg(Tos)-OH 13836-37-8 C18H28N4O6S
(1S,2R)-2-Amino-1,2-diphenylethanol (1S,2R)-2-Amino-1,2-diphenylethanol 23364-44-5 C14H15NO
L(+)-Ornithine hydrochloride L(+)-Ornithine hydrochloride 3184-13-2 C5H13ClN2O2
3-Amino-2-naphthoic acid 3-Amino-2-naphthoic acid 5959-52-4 C11H9NO2
L-Tyrosinol hydrochloride L-Tyrosinol hydrochloride 87745-27-5 C9H14ClNO2
H-TYR-NH2 HCL H-TYR-NH2 HCL 4985-46-0 C9H12N2O2
Methyl 1-aminocyclopropanecarboxylate hydrochloride Methyl 1-aminocyclopropanecarboxylate hydrochloride 72784-42-0 C5H10ClNO2
O-PHOSPHO-L-TYROSINE O-PHOSPHO-L-TYROSINE 21820-51-9 C9H12NO6P
(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID 262429-49-2 C9H10ClNO2
Fmoc-O-benzyl-L-serine Fmoc-O-benzyl-L-serine 83792-48-7 C25H23NO5
trans-1-Benzoyl-4-phenyl-L-proline trans-1-Benzoyl-4-phenyl-L-proline 120851-71-0 C18H17NO3
N-CARBOBENZOXY-L-SERINE BETA-LACTONE N-CARBOBENZOXY-L-SERINE BETA-LACTONE 26054-60-4 C11H11NO4
BOC-D-STYRYLALANINE DCHA SALT BOC-D-STYRYLALANINE DCHA SALT 261380-19-2 C16H21NO4
Glycine tert butyl ester hydrochloride Glycine tert butyl ester hydrochloride 27532-96-3 C6H14ClNO2
Poly(L-lysine hydrobromide) Poly(L-lysine hydrobromide) 25988-63-0 C6H14N2O2
L-Tyrosine Ethyl Ester Hydrochloride L-Tyrosine Ethyl Ester Hydrochloride 4089-07-0 C11H16ClNO3
1,2-Bis(bromomethyl)benzene 1,2-Bis(bromomethyl)benzene 91-13-4 C8H8Br2
(R)-N-Boc-(3-Pyridyl)alanine (R)-N-Boc-(3-Pyridyl)alanine 98266-33-2 C13H18N2O4
BOC-GAMMA-ABU-OH BOC-GAMMA-ABU-OH 57294-38-9 C9H17NO4
BETA-(2-THIENYL)-DL-ALANINE BETA-(2-THIENYL)-DL-ALANINE 2021-58-1 C7H9NO2S
BOC-D-PRO-OME BOC-D-PRO-OME 73323-65-6 C11H19NO4
BZ-GLU-OH BZ-GLU-OH 6094-36-6 C12H13NO5
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid 135042-12-5 C10H17NO5
Aceglutamide Aceglutamide 2490-97-3 C7H12N2O4
FMOC-2-NAL-OH FMOC-2-NAL-OH 112883-43-9 C28H23NO4
L-4-Iodophenylalanine L-4-Iodophenylalanine 24250-85-9 C9H10INO2
BOC-CYS(4-MEOBZL)-OH BOC-CYS(4-MEOBZL)-OH 18942-46-6 C16H23NO5S
FMOC-D-DAP(BOC)-OH FMOC-D-DAP(BOC)-OH 198544-42-2 C23H26N2O6
S-Methyl-L-cysteine S-Methyl-L-cysteine 1187-84-4 C4H9NO2S
H-GLU(OBZL)-OTBU HCL H-GLU(OBZL)-OTBU HCL 105590-97-4 C16H24ClNO4
DL-3-Aminobutyric acid DL-3-Aminobutyric acid 2835-82-7 C4H9NO2
N-Fmoc-N'-trityl-D-histidine N-Fmoc-N'-trityl-D-histidine 135610-90-1 C40H33N3O4
CBZ-BETA-AMINO-D-ALANINE CBZ-BETA-AMINO-D-ALANINE 62234-37-1 C11H14N2O4
N-Boc-2-piperidinecarboxylic acid N-Boc-2-piperidinecarboxylic acid 98303-20-9 C11H19NO4
L-LEUCYL-GLYCYL-GLYCINE L-LEUCYL-GLYCYL-GLYCINE 1187-50-4 C10H19N3O4
N-(p-Tolylsulphonyl)-L-glutamic acid N-(p-Tolylsulphonyl)-L-glutamic acid 4816-80-2 C12H15NO6S
BOC-(R)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-FLUORO-PHENYL)-BUTYRIC ACID 218608-98-1 C15H20FNO4
BOC-ARG-OH BOC-ARG-OH 13726-76-6 C11H22N4O4
1-METHYL-DL-TRYPTOPHAN 1-METHYL-DL-TRYPTOPHAN 26988-72-7 C12H14N2O2
L-Histidine hydrochloride L-Histidine hydrochloride 1007-42-7 C6H10ClN3O2
H-LEU-D-LEU-OH H-LEU-D-LEU-OH 17665-02-0 C12H24N2O3
L-BETA-HOMOSERINE L-BETA-HOMOSERINE 16504-56-6 C4H9NO3
4-FLUORO-DL-GLUTAMIC ACID 4-FLUORO-DL-GLUTAMIC ACID 2708-77-2 C5H8FNO4
BOC-THR(ME)-OH BOC-THR(ME)-OH 48068-25-3 C10H19NO5
H-D-ARG(NO2)-OME HCL H-D-ARG(NO2)-OME HCL 50912-92-0 C7H16ClN5O4
H-PHE-PNA HCL H-PHE-PNA HCL 2360-97-6 C15H15N3O3
3,4-DEHYDRO-DL-PROLINE 3,4-DEHYDRO-DL-PROLINE 3395-35-5 C5H7NO2
AMINO-(TETRAHYDRO-PYRAN-4-YL)-ACETIC ACID AMINO-(TETRAHYDRO-PYRAN-4-YL)-ACETIC ACID 53284-84-7 C7H13NO3
FMOC-GLY-OPFP FMOC-GLY-OPFP 86060-85-7 C23H14F5NO4
S-Cbz-L-cysteine S-Cbz-L-cysteine 1625-72-5 C11H13NO4S
6-METHYL-DL-TRYPTOPHAN 6-METHYL-DL-TRYPTOPHAN 2280-85-5 C12H14N2O2
(-)-ALPHA-[1-(DIBUTYLAMINO)ETHYL]BENZYL ALCOHOL (-)-ALPHA-[1-(DIBUTYLAMINO)ETHYL]BENZYL ALCOHOL 114389-70-7 C17H29NO
BOC-D-PHE(4-NHBOC)-OH BOC-D-PHE(4-NHBOC)-OH 214750-77-3 C29H30N2O6
(S)-3-AMINO-4-(4-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(4-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 270596-53-7 C10H12FNO2
BOC-N-ME-SER-OH BOC-N-ME-SER-OH 101772-29-6 C9H17NO5
ALPHA-METHYL-L-VALINE HYDROCHLORIDE ALPHA-METHYL-L-VALINE HYDROCHLORIDE 53940-83-3 C6H13NO2
PTH-VALINE PTH-VALINE 4333-20-4 C12H14N2OS
4-BORONO-L-PHENYLALANINE 4-BORONO-L-PHENYLALANINE 76410-58-7 C9H12BNO4
BOC-(S)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 270065-77-5 C16H20F3NO4
METHYL 3-AMINOBENZOATE METHYL 3-AMINOBENZOATE 4518-10-9 C8H9NO2
BOC-D-MEPHE-OH DCHA BOC-D-MEPHE-OH DCHA 102185-45-5 C27H44N2O4
DL-Asparagine monohydrate DL-Asparagine monohydrate 3130-87-8 C4H8N2O3
11-Aminoundecanoic acid 11-Aminoundecanoic acid 2432-99-7 C11H23NO2
Z-NVA-OH Z-NVA-OH 21691-44-1 C13H17NO4
P-AMINO-DL-PHENYLALANINE P-AMINO-DL-PHENYLALANINE 2922-41-0 C9H12N2O2
4-Dimethylaminobenzoic acid 4-Dimethylaminobenzoic acid 619-84-1 C9H11NO2
BOC-7-AMINO-HEPTANOIC ACID BOC-7-AMINO-HEPTANOIC ACID 60142-89-4 C12H23NO4
1-Boc-4-methylpiperidine-4-carboxylic acid 1-Boc-4-methylpiperidine-4-carboxylic acid 189321-63-9 C12H21NO4
Fmoc-N-methyl-L-phenylalanine Fmoc-N-methyl-L-phenylalanine 77128-73-5 C25H23NO4
Boc-3-Aminomethylbenzoic acid Boc-3-Aminomethylbenzoic acid 117445-22-4 C13H17NO4
N-Cbz-L-histidine N-Cbz-L-histidine 14997-58-1 C14H15N3O4
DL-2'-METHYLPHENYLALANINE HYDROCHLORIDE DL-2'-METHYLPHENYLALANINE HYDROCHLORIDE 22888-51-3 C10H13NO2
(2-FLUOROPHENYL)GLYCINE (2-FLUOROPHENYL)GLYCINE 2343-27-3 C8H8FNO2
N-CARBOBENZOXY-DL-NORVALINE N-CARBOBENZOXY-DL-NORVALINE 21691-43-0 C13H17NO4
4-Methoxy-L-phenylalanine 4-Methoxy-L-phenylalanine 6230-11-1 C10H13NO3
L-Aspartic acid 4-benzyl ester L-Aspartic acid 4-benzyl ester 2177-63-1 C11H13NO4
Fmoc-L-beta-homoalanine Fmoc-L-beta-homoalanine 193954-26-6 C19H19NO4
N-Benzyloxycarbonyl-D-aspartic acid N-Benzyloxycarbonyl-D-aspartic acid 78663-07-7 C12H13NO6
H-ASP(OBZL)-OBZL HCL H-ASP(OBZL)-OBZL HCL 6327-59-9 C18H20ClNO4
N-6-Trifluoroacetyl-L-lysine N-6-Trifluoroacetyl-L-lysine 10009-20-8 C8H13F3N2O3
N-ALPHA-BENZOYL-L-ARGININE N-ALPHA-BENZOYL-L-ARGININE 154-92-7 C13H18N4O3
(S)-TERT-LEUCINOL (S)-TERT-LEUCINOL 112245-13-3 C6H15NO
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