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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
Sodium N-dodecanoyl-L-alaninate Sodium N-dodecanoyl-L-alaninate 55535-58-5 C15H28NNaO3
Sodium N-dodecanoyl-L-phenlyalaninate Sodium N-dodecanoyl-L-phenlyalaninate 37869-82-2 C21H32NNaO3
N-Dodecanoyl-L-phenlyalanine N-Dodecanoyl-L-phenlyalanine 14379-64-7 C21H33NO3
NEPSILON-FMOC-NALPHA-CBZ-L-LYSINE, 98 NEPSILON-FMOC-NALPHA-CBZ-L-LYSINE, 98 105751-18-6 C29H30N2O6
N(ALPHA)-FMOC-N(EPSILON)-DABCYL-L-LYSINE N(ALPHA)-FMOC-N(EPSILON)-DABCYL-L-LYSINE 146998-27-8 C36H37N5O5
L-Isoleucine hydrochloride L-Isoleucine hydrochloride 17694-98-3 C6H14ClNO2
BOC-D-LEUCINOL  97 BOC-D-LEUCINOL 97 142121-48-0 C11H23NO3
FMOC-D-ALLO-THR(TBU)-OH FMOC-D-ALLO-THR(TBU)-OH 170643-02-4 C23H27NO5
(2S,4S)-4-METHYLGLUTAMIC ACID (2S,4S)-4-METHYLGLUTAMIC ACID 6141-27-1 C6H11NO4
BOC-GLU-GLU-LEU-OME BOC-GLU-GLU-LEU-OME 72903-33-4 C22H37N3O10
(S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE 6216-63-3 C13H17NO3
H-ALA-AMC H-ALA-AMC 77471-41-1 C13H14N2O3
Fmoc-3-iodo-L-phenylalanine Fmoc-3-iodo-L-phenylalanine 210282-31-8 C24H20INO4
(R)-N-ACETYL-3,4-DIMETHOXYPHENYLALANINE (R)-N-ACETYL-3,4-DIMETHOXYPHENYLALANINE 33043-37-7 C13H17NO5
H-TYR-OBZL H-TYR-OBZL 52799-86-7 C23H23NO3
AC-LYS(Z)-OH AC-LYS(Z)-OH 6367-08-4 C16H22N2O5
DL-N-BENZOYL-2-ISOPROPYLSERINE DL-N-BENZOYL-2-ISOPROPYLSERINE 52421-46-2 C13H17NO4
N-ALPHA-METHYL-D-VALINE HYDROCHLORIDE N-ALPHA-METHYL-D-VALINE HYDROCHLORIDE 210830-32-3 C6H14ClNO2
N-ME-ALA-OTBU HCL N-ME-ALA-OTBU HCL 103614-40-0 C8H18ClNO2
BOC-N-ME-THR-OH BOC-N-ME-THR-OH 101759-72-2 C10H19NO5
FMOC-BETA-(2-QUINOLYL)-D-ALA-OH FMOC-BETA-(2-QUINOLYL)-D-ALA-OH 214852-58-1 C27H22N2O4
N-BOC-ALPHA-METHYL-L-PROLINE N-BOC-ALPHA-METHYL-L-PROLINE 103336-06-7 C11H19NO4
Z-HYP(TBU)-OH Z-HYP(TBU)-OH 85201-91-8 C17H23NO5
BOC-(S)-3-AMINO-4-(4-TERT-BUTYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(4-TERT-BUTYL-PHENYL)-BUTYRIC ACID 403661-85-8 C19H29NO4
BOC-4-NITRO-L-PHENYLALANINE BOC-4-NITRO-L-PHENYLALANINE 103451-56-5 C14H18N2O6
AC-ALA-PNA AC-ALA-PNA 35978-75-7 C11H13N3O4
PD 166793 PD 166793 199850-67-4 C17H18BrNO4S
D-(-)-3-thienylglycine D-(-)-3-thienylglycine 1194-86-1 C6H7NO2S
1,2,4-triazolyl-3-alanine 1,2,4-triazolyl-3-alanine 10109-05-4 C5H8N4O2
3,4-Difluoro-D-phenylalanine 3,4-Difluoro-D-phenylalanine 249648-08-6 C9H9F2NO2
2-Methoxy-L-phenylalanine 2-Methoxy-L-phenylalanine 193546-31-5 C10H13NO3
Ethyl 2-(acetylamino)-3-[3,5-diiodo-4-(4-methoxyphenoxy)phenyl]propanoate Ethyl 2-(acetylamino)-3-[3,5-diiodo-4-(4-methoxyphenoxy)phenyl]propanoate 83249-56-3 C20H21I2NO5
N-Acetyl-3-chloro-L-serine methyl ester N-Acetyl-3-chloro-L-serine methyl ester 87333-22-0 C6H10ClNO3
D-2-Thiolhistidine D-2-Thiolhistidine 1195264-93-7 C6H9N3O2S
fmoc-D-2,4-dichlorophenylalanine fmoc-D-2,4-dichlorophenylalanine 352351-61-2 C24H19Cl2NO4
3-(2-Pyrrolyl)-DL-alanine 3-(2-Pyrrolyl)-DL-alanine 3078-36-2 C7H10N2O2
D-4-Bromophenylglycine D-4-Bromophenylglycine C8H8BrNO2
DL-Cyclobutylglycine DL-Cyclobutylglycine 28024-69-3 C6H11NO2
N-BOC-(1R,2R)-(-)-2-AMINO-1-(4-NITROPHE& N-BOC-(1R,2R)-(-)-2-AMINO-1-(4-NITROPHE& 366487-74-3 C14H20N2O6
Ethyl N-(2,3-dichloro-6-aminobenzyl)glcycine Ethyl N-(2,3-dichloro-6-aminobenzyl)glcycine 70406-92-7 C11H14Cl2N2O2
Boc-D-2,4-Dichlorophenylalanine Boc-D-2,4-Dichlorophenylalanine 114873-2-0
(1R,2R)-(-)-2-Amino-1-cyclopentanecarboxylic acid (1R,2R)-(-)-2-Amino-1-cyclopentanecarboxylic acid 136315-77-0 C6H11NO2
1-Methyl-5-oxo-D-proline methyl ester 1-Methyl-5-oxo-D-proline methyl ester 122742-14-7 C7H11NO3
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)- (9CI) Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)- (9CI) 746657-36-3 C8H13NO2
DL-METHIONINOL DL-METHIONINOL 502-83-0 C5H13NOS
D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) 178962-09-9 C6H11NO3
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, (1R,2S)- (9CI) Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, (1R,2S)- (9CI) 159700-58-0 C6H9NO2
N-alpha-Methyl-L-lysinehydrochloride N-alpha-Methyl-L-lysinehydrochloride 7431-89-2 C7H16N2O2
1-N-BENZYL-PROLINE
1-N-BENZYL-PROLINE 60169-72-4 C12H15NO2
L-4'-TETRAHYDROPYRANYLGLYCINE
L-4'-TETRAHYDROPYRANYLGLYCINE 811842-25-8 C7H13NO3
Carbobenzoxy-D,L-tryptophanamide Carbobenzoxy-D,L-tryptophanamide 27018-75-3 C19H19N3O3
FMOC-ARG(MTR)-OPFP FMOC-ARG(MTR)-OPFP 130397-19-2 C37H35F5N4O7S
S-SULFO-L-CYSTEINE SODIUM SALT S-SULFO-L-CYSTEINE SODIUM SALT 1637-71-4 C3H7NO5S2
GLYCINE N-PENTYL ESTER HYDROCHLORIDE GLYCINE N-PENTYL ESTER HYDROCHLORIDE 203302-88-9 C7H16ClNO2
BOC-8-AMINOCAPRYLIC ACID BOC-8-AMINOCAPRYLIC ACID 30100-16-4 C13H25NO4
Z-PRO-ARG-AMC HCL Z-PRO-ARG-AMC HCL 70375-23-4 C29H35ClN6O6
5-METHYL-DL-TRYPTOPHAN HYDRATE 5-METHYL-DL-TRYPTOPHAN HYDRATE 207556-14-7 C12H16N2O3
FMOC-GLU(OCHX)-OH FMOC-GLU(OCHX)-OH 150047-85-1 C26H29NO6
L-Norvaline, 5-hydroxy-N-[(phenylmethoxy)carbonyl]-, 1-methylethyl ester L-Norvaline, 5-hydroxy-N-[(phenylmethoxy)carbonyl]-, 1-methylethyl ester 176237-44-8 C16H23NO5
N-ETHOXYCARBONYL-L-PHENYLALANINE N-ETHOXYCARBONYL-L-PHENYLALANINE 19887-32-2 C12H15NO4
N,N-DIBENZYL-L-SERINE METHYL ESTER N,N-DIBENZYL-L-SERINE METHYL ESTER 88099-67-6 C18H21NO3
N-(3,5-DINITROBENZOYL)-DL-LEUCINE N-(3,5-DINITROBENZOYL)-DL-LEUCINE 74928-54-4 C13H15N3O7
Z-3-AMINOBUTYRIC ACID Z-3-AMINOBUTYRIC ACID 51440-81-4 C12H15NO4
4-NITRO-PHENYLALANINE METHYL ESTER 4-NITRO-PHENYLALANINE METHYL ESTER 85317-52-8 C10H12N2O4
N-Acetyl-L-asparagine N-Acetyl-L-asparagine 4033-40-3 C6H10N2O4
N-DICHLOROACETYL-D-SERINE SODIUM SALT N-DICHLOROACETYL-D-SERINE SODIUM SALT C5H6Cl2NNaO4
L-Threonine hydrochloride L-Threonine hydrochloride 82650-07-5 C4H10ClNO3
N(ALPHA)-LAUROYL-L-ARGININE* N(ALPHA)-LAUROYL-L-ARGININE* 42492-22-8 C18H36N4O3
N-BOC-ERYTHRO-D-BETA-METHYLPHENYLALANINE, 98 N-BOC-ERYTHRO-D-BETA-METHYLPHENYLALANINE, 98 198493-85-5 C15H21NO4
N-TRITYL-L-HOMOSERINE TRIETHYLAMINE SALT N-TRITYL-L-HOMOSERINE TRIETHYLAMINE SALT 102056-97-3 C29H38N2O3
DANSYL-D-PHENYLALANINE FREE ACID DANSYL-D-PHENYLALANINE FREE ACID 56176-31-9 C21H22N2O4S
L-TRYPTOPHAN BENZYL ESTER  98 L-TRYPTOPHAN BENZYL ESTER 98 4299-69-8 C18H18N2O2
BENZOTRIPT BENZOTRIPT 39544-74-6 C18H15ClN2O3
L-LYSINE MONO HCL L-LYSINE MONO HCL C6H15ClN2O2
KETOPROFEN LYSINATE SALT KETOPROFEN LYSINATE SALT
N-ME-D-ALA-OTBU HCL N-ME-D-ALA-OTBU HCL 405513-14-6 C8H17NO2
4-AMINO-1H-PYRROLE-2-CARBOXYLIC ACID 4-AMINO-1H-PYRROLE-2-CARBOXYLIC ACID 155815-95-5 C5H6N2O2
FMOC-LYS(TNM)-OH FMOC-LYS(TNM)-OH 251316-95-7 C32H39N3O10
4-AMINO-3-METHOXY-PIPERIDINE-ETHYLCARBAMATE 4-AMINO-3-METHOXY-PIPERIDINE-ETHYLCARBAMATE 86717-62-6 C9H18N2O3
S-ADENOSYL-L-METHIONINE DISULFATE TOSYLATE S-ADENOSYL-L-METHIONINE DISULFATE TOSYLATE C29H42N6O19S5
(RS)-3-CARBOXY-4-HYDROXYPHENYLGLYCINE (RS)-3-CARBOXY-4-HYDROXYPHENYLGLYCINE 64043-84-1 C9H9NO5
FMOC-D-ASP-ODMB FMOC-D-ASP-ODMB 200335-63-3 C28H27NO8
FMOC-ISONIPECOTIC ACID FMOC-ISONIPECOTIC ACID 148928-15-8 C21H21NO4
DL-ALANINE-OBZL P-TOSYLATE DL-ALANINE-OBZL P-TOSYLATE 46229-47-4 C10H13NO2
4-[CARBOXY-(4-METHOXY-PHENYL)-METHYL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER HYDROCHLORIDE 4-[CARBOXY-(4-METHOXY-PHENYL)-METHYL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER HYDROCHLORIDE 868260-17-7 C18H26N2O5
L-Arginine DL-Malate(2:1) L-Arginine DL-Malate(2:1)
N-Acetyl-L-Hydroxyproline N-Acetyl-L-Hydroxyproline 39966-33-7 C7H10NO4
Ethyl N-[[5-methyl-2-(isopropyl)cyclohexyl]carbonyl]glycinate Ethyl N-[[5-methyl-2-(isopropyl)cyclohexyl]carbonyl]glycinate 39668-74-1 C15H27NO3
1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester 1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester 37813-30-2 C12H21NO5
1-Amino-2-ethenylcyclopropanecarboxylicacid 1-Amino-2-ethenylcyclopropanecarboxylicacid 80003-54-9 C6H9NO2
L-Citrulline L-Malate 1:1 L-Citrulline L-Malate 1:1
N-Methyl-L-Cysteine N-Methyl-L-Cysteine C4H9NO2S
S-Allyl-D-Cysteine S-Allyl-D-Cysteine C6H11NO2S
D-2,5-Dichlorophenylalanine D-2,5-Dichlorophenylalanine 718596-54-4 C9H9Cl2NO2
D-2-(5-Bromothienyl)alanine D-2-(5-Bromothienyl)alanine 264903-54-0 C7H8BrNO2S
DL-2-Furylalanine DL-2-Furylalanine 4066-39-1 C7H9NO3
(S)-2-CBZ-AMINO-BUTANE-1,4-DIOL
(S)-2-CBZ-AMINO-BUTANE-1,4-DIOL 118219-23-1 C12H17NO4
(S)-N-[4'-BENZYL)PIPERIDINO]PROLINE
(S)-N-[4'-BENZYL)PIPERIDINO]PROLINE 669713-67-1 C17H24N2O2
N-Acetyl-S-(3-carboxy-1-methylpropyl)-L-cysteine N-Acetyl-S-(3-carboxy-1-methylpropyl)-L-cysteine 33164-65-7 C9H15NO5S
Fmoc-Lys(Trt)-OH Fmoc-Lys(Trt)-OH 719892-61-2 C40H38N2O4
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