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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
N-FORMYL-DL-TRYPTOPHAN N-FORMYL-DL-TRYPTOPHAN 16108-03-5 C12H12N2O3
(1R,2S)-1-Amino-2-indanol (1R,2S)-1-Amino-2-indanol 136030-00-7 C9H11NO
3-Dimethylaminopropane-1,2-diol 3-Dimethylaminopropane-1,2-diol 623-57-4 C5H13NO2
Fmoc-D-Asparagine Fmoc-D-Asparagine 108321-39-7 C19H18N2O5
Fmoc-3-(4-pyridyl)-L-alanine Fmoc-3-(4-pyridyl)-L-alanine 169555-95-7 C23H20N2O4
L-Glutamic acid 5-cyclohexyl ester L-Glutamic acid 5-cyclohexyl ester 112471-82-6 C11H19NO4
7-Aminoheptanoic acid 7-Aminoheptanoic acid 929-17-9 C7H15NO2
N-Boc-L-valine N-Boc-L-valine 13734-41-3 C10H19NO4
Teriparatide acetate Teriparatide acetate 52232-67-4 C172H278N52O47S2
FMOC-LYS(DNP)-OH FMOC-LYS(DNP)-OH 148083-64-1 C27H26N4O8
L-Ser-OBzl.HCl L-Ser-OBzl.HCl 60022-62-0 C10H14ClNO3
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE 131818-17-2 C11H14BrNO2
O-Benzyl-L-tyrosine benzyl ester hydrochloride O-Benzyl-L-tyrosine benzyl ester hydrochloride 52142-01-5 C23H24ClNO3
AC-LYS-OH AC-LYS-OH 1946-82-3 C8H16N2O3
5-Hydroxymethylpyrrolidin-2-one 5-Hydroxymethylpyrrolidin-2-one 66673-40-3 C5H9NO2
L-4-THIAZOLYLALANINE L-4-THIAZOLYLALANINE 119433-80-6 C6H8N2O2S
Boc-4-Amino-D-phenylalanine Boc-4-Amino-D-phenylalanine 164332-89-2 C14H20N2O4
Boc-3,3-Diphenyl-L-alanine Boc-3,3-Diphenyl-L-alanine 138662-63-2 C20H23NO4
1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate 1-(1,1-Dimethylethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate 203866-14-2 C10H16FNO4
D-2-Aminobutyric acid D-2-Aminobutyric acid 2623-91-8 C4H9NO2
L-Cysteine methyl ester hydrochloride L-Cysteine methyl ester hydrochloride 18598-63-5 C4H10ClNO2S
BOC-D-3-Trifluoromethylphe BOC-D-3-Trifluoromethylphe 82317-82-6 C15H18F3NO4
Z-ARG(Z)2-OH Z-ARG(Z)2-OH 14611-34-8 C30H32N4O8
BOC-HIS(Z)-OH BOC-HIS(Z)-OH 50305-43-6 C19H23N3O6
3,3-Diphenyl-L-alanine 3,3-Diphenyl-L-alanine 149597-92-2 C15H15NO2
D-LEUCYL-GLYCYL-GLYCINE D-LEUCYL-GLYCYL-GLYCINE 18625-22-4 C10H19N3O4
Boc-3-(2-thienyl)-L-alanine Boc-3-(2-thienyl)-L-alanine 56675-37-7 C12H17NO4S
3-AMINO-2,5,6-TRIFLUOROBENZOIC ACID 3-AMINO-2,5,6-TRIFLUOROBENZOIC ACID 133622-65-8 C7H4F3NO2
FMOC-L-Valine FMOC-L-Valine 68858-20-8 C20H21NO4
1-Amino-1-cyclohexanecarboxylic acid 1-Amino-1-cyclohexanecarboxylic acid 2756-85-6 C7H13NO2
4-Methylphenyl-L-alanine 4-Methylphenyl-L-alanine 1991-87-3 C10H13NO2
BOC-(S)-3-AMINO-4-(4-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(4-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 270065-80-0 C16H20F3NO4
L-Glutamic acid 5-methyl ester L-Glutamic acid 5-methyl ester 1499-55-4 C6H11NO4
tert-Butyl 3-phenyl-L-alaninate hydrochloride tert-Butyl 3-phenyl-L-alaninate hydrochloride 15100-75-1 C13H20ClNO2
Boc-beta-alanine Boc-beta-alanine 3303-84-2 C8H15NO4
BOC-D-4-Fluorophe BOC-D-4-Fluorophe 57292-45-2 C14H18FNO4
D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE D-ASPARTIC ACID DIMETHYL ESTER HYDROCHLORIDE 69630-50-8 C6H12ClNO4
Methyl L-argininate dihydrochloride Methyl L-argininate dihydrochloride 26340-89-6 C7H18Cl2N4O2
2-Hydroxy-4-amino butanoic acid 2-Hydroxy-4-amino butanoic acid 13477-53-7 C4H9NO3
DL-4-HYDROXYPHENYLGLYCINE DL-4-HYDROXYPHENYLGLYCINE 938-97-6 C8H9NO3
DL-Lysine monohydrochloride DL-Lysine monohydrochloride 70-53-1 C6H14N2O2.ClH
L-Tyrosine benzyl ester p-toluenesulfonate L-Tyrosine benzyl ester p-toluenesulfonate 53587-11-4 C23H25NO6S
1-Hydroxybenzotriazole 1-Hydroxybenzotriazole 2592-95-2 C6H5N3O
Boc-L-Histidine(Tosyl) Boc-L-Histidine(Tosyl) 35899-43-5 C18H23N3O6S
N-Boc-N'-(2-chlorobenzyloxycarbonyl)-L-lysine N-Boc-N'-(2-chlorobenzyloxycarbonyl)-L-lysine 54613-99-9 C19H27ClN2O6
tert-Butyl L-prolinate hydrochloride tert-Butyl L-prolinate hydrochloride 5497-76-7 C9H18ClNO2
3-FLUORO-L-TYROSINE 3-FLUORO-L-TYROSINE 7423-96-3 C9H10FNO3
BOC-D-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID BOC-D-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID 123910-26-9 C17H20N2O4
N-alpha-Cbz-L-lysine N-alpha-Cbz-L-lysine 2212-75-1 C14H20N2O4
BOC-L-4-Methylphe BOC-L-4-Methylphe 80102-26-7 C15H21NO4
DL-4-Chlorophenylalanine methyl ester hydrochloride DL-4-Chlorophenylalanine methyl ester hydrochloride 14173-40-1 C10H13Cl2NO2
(-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID (-)-(1S,4R)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID 151907-79-8 C11H17NO4
L-2,4-DICHLOROPHENYLALANINE L-2,4-DICHLOROPHENYLALANINE 111119-36-9 C9H9Cl2NO2
L-2-FURYLALANINE L-2-FURYLALANINE 127682-08-0 C7H9NO3
Oxaceprol Oxaceprol 33996-33-7 C7H11NO4
4-(Methylamino)benzoic acid 4-(Methylamino)benzoic acid 10541-83-0 C8H9NO2
D-4,4'-BIPHENYLALANINE D-4,4'-BIPHENYLALANINE 170080-13-4 C15H15NO2
N-Acetylglycine N-Acetylglycine 543-24-8 C4H7NO3
H-D-PHG-OME HCL H-D-PHG-OME HCL 19883-41-1 C9H12ClNO2
(R)-N-BOC-2-Bromophenylalanine (R)-N-BOC-2-Bromophenylalanine 261360-76-3 C14H18BrNO4
BOC-D-DAB(FMOC)-OH BOC-D-DAB(FMOC)-OH 131570-57-5 C24H28N2O6
TOS-ARG-OME HCL TOS-ARG-OME HCL 1784-03-8 C14H23ClN4O4S
(S)-N-BOC-2-Bromophenylalanine (S)-N-BOC-2-Bromophenylalanine 261165-02-0 C14H18BrNO4
4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER 4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER 183673-66-7 C26H30N2O6
3-AMINOPHTHALIC ACID 3-AMINOPHTHALIC ACID 5434-20-8 C8H7NO4
(S)-N-Boc-allylglycine (S)-N-Boc-allylglycine 90600-20-7 C10H17NO4
(R)-3-Amino-1,2-propanediol (R)-3-Amino-1,2-propanediol 66211-46-9 C3H9NO2
Fmoc-O-trityl-L-threonine Fmoc-O-trityl-L-threonine 133180-01-5 C38H33NO5
Boc-D-Allylglycine Boc-D-Allylglycine 170899-08-8 C10H17NO4
DL-Pyroglutamic acid DL-Pyroglutamic acid 149-87-1 C5H7NO3
BENZOYL-DL-LEUCINE BENZOYL-DL-LEUCINE 17966-67-5 C13H17NO3
BOC-L-4,4'-BIPHENYLALANINE BOC-L-4,4'-BIPHENYLALANINE 147923-08-8 C20H23NO4
N-Cbz-L-Aspartic acid 4-benzyl ester N-Cbz-L-Aspartic acid 4-benzyl ester 3479-47-8 C19H19NO6
AC-D-PRO-OH AC-D-PRO-OH 59785-68-1 C7H11NO3
Boc-D-Valine Boc-D-Valine 22838-58-0 C10H19NO4
Fmoc-D-Asn(Trt)-OH Fmoc-D-Asn(Trt)-OH 180570-71-2 C38H32N2O5
H-TYR(BZL)-OH H-TYR(BZL)-OH 16652-64-5 C16H17NO3
BOC-L-3-CYANOPHENYLALANINE BOC-L-3-CYANOPHENYLALANINE 131980-30-8 C15H18N2O4
BOC-PHE(4-NHFMOC)-OH BOC-PHE(4-NHFMOC)-OH 114346-31-5 C29H30N2O6
FMOC-L-Arginine FMOC-L-Arginine 91000-69-0 C21H24N4O4
D-(-)-A-4-HYDROXYPHENYLGLYCINE DANE SALT METHYL POTASSIUM D-(-)-A-4-HYDROXYPHENYLGLYCINE DANE SALT METHYL POTASSIUM 69416-61-1 C13H16KNO5
Nalpha-Cbz-L-Arginine Nalpha-Cbz-L-Arginine 1234-35-1 C14H20N4O4
Methyl L-pyroglutamate Methyl L-pyroglutamate 4931-66-2 C6H9NO3
H-D-MET-OME HCL H-D-MET-OME HCL 69630-60-0 C6H14ClNO2S
L(+)-Leucinol L(+)-Leucinol 7533-40-6 C6H15NO
L-Cyclopropylglycine L-Cyclopropylglycine 49606-99-7 C5H9NO2
Fmoc-D-glutamic acid gamma-tert-butyl ester Fmoc-D-glutamic acid gamma-tert-butyl ester 104091-08-9 C24H27NO6
D-Tyrosinol hydrochloride D-Tyrosinol hydrochloride 40829-04-7 C9H14ClNO2
L-Homoserine L-Homoserine 672-15-1 C4H9NO3
Ornipressin Ornipressin 3397-23-7 C45H63N13O12S2
BOC-D-PRO-OSU BOC-D-PRO-OSU 102185-34-2 C14H20N2O6
Rink Amide Linker Rink Amide Linker 145069-56-3 C32H29NO7
N-Acetyl-L-isoleucine N-Acetyl-L-isoleucine 3077-46-1 C8H15NO3
Z-D-ASP(OTBU)-OH H2O Z-D-ASP(OTBU)-OH H2O 71449-08-6 C16H21NO6
BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(4-FLUORO-PHENYL)-BUTYRIC ACID 218608-97-0 C15H20FNO4
Methyl L-prolinate hydrochloride Methyl L-prolinate hydrochloride 2133-40-6 C6H12ClNO2
L-Pyroglutaminol L-Pyroglutaminol 17342-08-4 C5H9NO2
BOC-MET(O)-OH BOC-MET(O)-OH 34805-21-5 C10H19NO5S
Fmoc-D-tryptophan Fmoc-D-tryptophan 86123-11-7 C26H22N2O4
N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline N2-1[(1S)-Ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysyl-L-proline 103300-91-0 C25H34F3N3O6
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