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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-Methyl-L-Cysteine N-Methyl-L-Cysteine C4H9NO2S
S-Allyl-D-Cysteine S-Allyl-D-Cysteine C6H11NO2S
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
FMOC-ISONIPECOTIC ACID FMOC-ISONIPECOTIC ACID 148928-15-8 C21H21NO4
DL-ALANINE-OBZL P-TOSYLATE DL-ALANINE-OBZL P-TOSYLATE 46229-47-4 C10H13NO2
FMOC-D-ASP-ODMB FMOC-D-ASP-ODMB 200335-63-3 C28H27NO8
(RS)-3-CARBOXY-4-HYDROXYPHENYLGLYCINE (RS)-3-CARBOXY-4-HYDROXYPHENYLGLYCINE 64043-84-1 C9H9NO5
S-ADENOSYL-L-METHIONINE DISULFATE TOSYLATE S-ADENOSYL-L-METHIONINE DISULFATE TOSYLATE C29H42N6O19S5
L-LYSINE MONO HCL L-LYSINE MONO HCL C6H15ClN2O2
KETOPROFEN LYSINATE SALT KETOPROFEN LYSINATE SALT
4-AMINO-1H-PYRROLE-2-CARBOXYLIC ACID 4-AMINO-1H-PYRROLE-2-CARBOXYLIC ACID 155815-95-5 C5H6N2O2
N-ME-D-ALA-OTBU HCL N-ME-D-ALA-OTBU HCL 405513-14-6 C8H17NO2
4-AMINO-3-METHOXY-PIPERIDINE-ETHYLCARBAMATE 4-AMINO-3-METHOXY-PIPERIDINE-ETHYLCARBAMATE 86717-62-6 C9H18N2O3
FMOC-LYS(TNM)-OH FMOC-LYS(TNM)-OH 251316-95-7 C32H39N3O10
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
2,3,4-Trifluoro-L-phenylalanine 2,3,4-Trifluoro-L-phenylalanine 873429-58-4 C9H8F3NO2
(S)-3-(Boc-amino)-4-(3-chlorophenyl)butyric acid (S)-3-(Boc-amino)-4-(3-chlorophenyl)butyric acid C15H20ClNO4
S-N-[(1-Ethoxycarbony1-3-Oxo-3-Phenylpropyl)]-L-Alanine S-N-[(1-Ethoxycarbony1-3-Oxo-3-Phenylpropyl)]-L-Alanine C15H19NO5
D-Cysteine ethyl ester hydrochloride D-Cysteine ethyl ester hydrochloride C5H12ClNO2S
Dihydrophenylglycine base Dihydrophenylglycine base
5-Methyl-D-tryptophan 5-Methyl-D-tryptophan 99295-79-1 C12H14N2O2
Boc-L-Alanine N-carboxyanhydride Boc-L-Alanine N-carboxyanhydride
Fmoc-2,4-Difluoro-D-Phenylalanine Fmoc-2,4-Difluoro-D-Phenylalanine C24H19F2NO4
5-Pyrimidinecarboxylicacid,2-amino-4-(trifluoromethyl)-(9CI) 5-Pyrimidinecarboxylicacid,2-amino-4-(trifluoromethyl)-(9CI) 149771-23-3 C6H4F3N3O2
glycohyodeoxycholic acid glycohyodeoxycholic acid 13042-33-6 C26H43NO5
N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine N-9-fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine 150308-80-8 C26H25NO5Se
H-D-CHG-OME HCL H-D-CHG-OME HCL 14328-64-4 C9H18ClNO2
L-β-Homo-Val-OH.HCl L-β-Homo-Val-OH.HCl 402587-64-8 C6H13NO2.ClH
H-Glu(OtBu)-OBzl.HCl H-Glu(OtBu)-OBzl.HCl 98102-32-0 C16H24ClNO4
H-D-Me-Val-OH H-D-Me-Val-OH 88930-14-7 C6H13NO2
Z-N-Methyl-D-valine Z-N-Methyl-D-valine 53978-73-7 C14H19NO4
N-[(2-Methyl-1H-benzimidazol-1-yl)acetyl]-L-phenylalanine N-[(2-Methyl-1H-benzimidazol-1-yl)acetyl]-L-phenylalanine 40332-25-0 C19H19N3O3
N-ME-PHE-OBZL P-TOSYLATE N-ME-PHE-OBZL P-TOSYLATE 40298-25-7 C24H27NO5S
FMOC-OIC-OH FMOC-OIC-OH 130309-37-4 C24H25NO4
BOC-3-(1-PYRENYL)-D-ALANINE BOC-3-(1-PYRENYL)-D-ALANINE 126613-96-5 C24H23NO4
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
GLUTAMINASE GLUTAMINASE 9001-47-2
N-Acetyl-L-asparagine N-Acetyl-L-asparagine 4033-40-3 C6H10N2O4
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
BOC-DL-7-AZATRYPTOPHAN BOC-DL-7-AZATRYPTOPHAN 129423-33-2 C15H19N3O4
7-BROMO-L-TRYPTOPHAN 7-BROMO-L-TRYPTOPHAN 75816-19-2 C11H11BrN2O2
L-Norvaline, 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-, 1-methylethyl ester L-Norvaline, 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-, 1-methylethyl ester 176237-45-9 C17H25NO7S
(r,s)-2-Amino-3-[3-(carboxymethoxy)-5-methyl-isoxazol-4 -yl]-propionic Acid Sesquihydrate (r,s)-2-Amino-3-[3-(carboxymethoxy)-5-methyl-isoxazol-4 -yl]-propionic Acid Sesquihydrate 209977-56-0 C18H30N4O15
(S)-3-(benzylamino)-2-(benzyloxycarbonylamino)propanoic acid (S)-3-(benzylamino)-2-(benzyloxycarbonylamino)propanoic acid 160885-24-5 C18H20N2O4
MACULOSIN MACULOSIN 4549-02-4 C14H16N2O3
FMOC-GLN(1-ADAMANTYL)-OH FMOC-GLN(1-ADAMANTYL)-OH 159926-84-8 C30H34N2O5
DL-GLUTAMIC-2,4,4-D3 ACID DL-GLUTAMIC-2,4,4-D3 ACID 96927-56-9 C5H9NO4
O-(2-AMINOETHYL)-L-SERINE HYDROCHLORIDE O-(2-AMINOETHYL)-L-SERINE HYDROCHLORIDE 118021-35-5 C5H13ClN2O3
N-([3-(TRIFLUOROMETHYL)PHENYL]SULFONYL)VALINE N-([3-(TRIFLUOROMETHYL)PHENYL]SULFONYL)VALINE 250714-85-3 C12H14F3NO4S
FMOC-3,4-DICHLORO-L-PHENYLALANINE FMOC-3,4-DICHLORO-L-PHENYLALANINE 17766-59-5 C13H17ClO4
(S)-2-AMINO-5-(1,3-DIOXOLAN-2-YL)-PENTANOIC ACID (S)-2-AMINO-5-(1,3-DIOXOLAN-2-YL)-PENTANOIC ACID 215054-80-1 C8H15NO4
D-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER HCL D-(-)-2-CHLOROPHENYLGLYCINE METHYL ESTER HCL 212838-70-5 C9H11Cl2NO2
BOC-PHE-ONP BOC-PHE-ONP 7535-56-0 C20H22N2O6
FMOC-(S)-2-THIENYLGLYCINE FMOC-(S)-2-THIENYLGLYCINE 211682-13-2 C21H17NO4S
ALX 5407 HYDROCHLORIDE ALX 5407 HYDROCHLORIDE 571147-18-7 C24H24FNO3
Noopept Noopept 157115-85-0 C17H22N2O4
FMOC-D-HOCIT-OH FMOC-D-HOCIT-OH 201485-38-3 C22H25N3O5
LEUCINE ENKEPHALIN ACETATE SALT LEUCINE ENKEPHALIN ACETATE SALT 81678-16-2 C30H41N5O9
N-tert-Butoxycarbonyl-3-mercapto-L-valine N-tert-Butoxycarbonyl-3-mercapto-L-valine 110763-40-1 C10H19NO4S
Gonadorelin acetate Gonadorelin acetate 34973-08-5 C57H79N17O15
N-ACETYL-S-(3,4-DIHYDROXYBUTYL)-L-CYSTEINE N-ACETYL-S-(3,4-DIHYDROXYBUTYL)-L-CYSTEINE 144889-50-9 C9H17NO5S
L-ASPARTIC ACID BETA-HYDROXAMATE L-ASPARTIC ACID BETA-HYDROXAMATE 1955-68-6 C4H8N2O4
(R)-2-TERT-BUTOXYCARBONYLAMINO-3-CYCLOPENTYL-PROPIONIC ACID (R)-2-TERT-BUTOXYCARBONYLAMINO-3-CYCLOPENTYL-PROPIONIC ACID 219819-74-6 C13H23NO4
7-CHLORO-L-TRYPTOPHAN 7-CHLORO-L-TRYPTOPHAN 73945-46-7 C11H11ClN2O2
L-gamma-Glutamyl-S-(phenylmethyl)-L-cysteinyl-2-phenylglycine diethyl ester monohydrochloride L-gamma-Glutamyl-S-(phenylmethyl)-L-cysteinyl-2-phenylglycine diethyl ester monohydrochloride 286942-97-0 C27H35N3O6S.ClH
N-Benzyl-DL-serine Methyl Ester N-Benzyl-DL-serine Methyl Ester 144001-42-3 C11H15NO3
N-[(Phenylmethoxy)carbonyl]-N-(phenylmethyl)-beta-alanine N-[(Phenylmethoxy)carbonyl]-N-(phenylmethyl)-beta-alanine 252919-08-7 C18H19NO4
(S)-(-)-2-AMINO-4-METHYL-1,1-DIPHENYL-1-PENTANOL (S)-(-)-2-AMINO-4-METHYL-1,1-DIPHENYL-1-PENTANOL 78603-97-1 C18H23NO
FMOC-D-ARG(MTS)-OH FMOC-D-ARG(MTS)-OH 268204-88-2 C30H34N4O6S
CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID CIS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID 5691-20-3 C7H13NO2
N-Boc-N-methyl glycine methyl ester N-Boc-N-methyl glycine methyl ester 42492-57-9 C9H17NO4
D-2,4,5-TRIFLUOROPHE D-2,4,5-TRIFLUOROPHE C9H8F3NO2
N<T/(IM)>-TRITYL-L-HISTIDINE-PROPYLAMIDE N-TRITYL-L-HISTIDINE-PROPYLAMIDE 171176-63-9 C28H30N4O
N(ALPHA)-(2 4-DINITRO-5-FLUOROPHENYL)- N(ALPHA)-(2 4-DINITRO-5-FLUOROPHENYL)- 210529-62-7 C11H13FN4O5
(S)-BOC-BETA-TYR-OH (S)-BOC-BETA-TYR-OH 499995-80-1 C14H19NO5
N-BENZOYL-DL-THREONINE N-BENZOYL-DL-THREONINE 7469-23-0 C11H13NO4
LS-TETRASACCHARIDE A LS-TETRASACCHARIDE A 64003-53-8 C37H62N2O29
FMOC-STA-OH FMOC-STA-OH 158257-40-0 C23H27NO5
BAA BAA 965-03-7 C13H19N5O2
H-PRA-OME HCL H-PRA-OME HCL 166271-28-9 C6H10ClNO2
DL-Cyclopropylalanine DL-Cyclopropylalanine C6H11NO2
diethyl N-[4-(methylamino)benzoyl]-L-glutamate diethyl N-[4-(methylamino)benzoyl]-L-glutamate 2378-95-2 C17H24N2O5
diammonium [N,N-bis[2-[bis(carboxymethyl)amino]ethyl]glycinato(5-)]ferrate(2-) diammonium [N,N-bis[2-[bis(carboxymethyl)amino]ethyl]glycinato(5-)]ferrate(2-) 85959-68-8 C14H22FeN4O10-
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, methyl ester, (1R,2S)- (9CI) Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, methyl ester, (1R,2S)- (9CI) 681260-04-8 C7H11NO2
FMOC-LYS(MEABZ-BOC)-OH FMOC-LYS(MEABZ-BOC)-OH 251103-43-2 C34H39N3O7
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