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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
2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 2-HYDROXYMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 170491-63-1 C10H19NO3
3-AMINO-3-PHENYL-1-PROPANOL 3-AMINO-3-PHENYL-1-PROPANOL 14593-04-5 C9H13NO
H-ILE-NH2 HCL H-ILE-NH2 HCL 10466-56-5 C6H15ClN2O
H-PRO-OTBU H-PRO-OTBU 2812-46-6 C9H17NO2
H-PHE-NH2 H-PHE-NH2 5241-58-7 C9H12N2O
2-Amino-2-methyl-1,3-propanediol 2-Amino-2-methyl-1,3-propanediol 115-69-5 C4H11NO2
H-ASP(OET)-OET HCL H-ASP(OET)-OET HCL 16115-68-7 C8H16ClNO4
H-His(Trt)-OH H-His(Trt)-OH 35146-32-8 C25H23N3O2
N-alpha-Boc-L-tryptophanol N-alpha-Boc-L-tryptophanol 82689-19-8 C16H22N2O3
FMOC-GLU(OALL)-OH FMOC-GLU(OALL)-OH 133464-46-7 C23H23NO6
BOC-D-2-Fluorophe BOC-D-2-Fluorophe 114873-10-8 C14H18FNO4
N-Acetyl-L-leucine N-Acetyl-L-leucine 1188-21-2 C8H15NO3
Fmoc-p(NH-Boc)-L-Phe-OH Fmoc-p(NH-Boc)-L-Phe-OH 174132-31-1 C29H30N2O6
AC-D-ALA-OH AC-D-ALA-OH 19436-52-3 C5H9NO3
3-FLUORO-L-PHENYLALANINE 3-FLUORO-L-PHENYLALANINE 19883-77-3 C9H10FNO2
N-Cbz-L-serine methyl ester N-Cbz-L-serine methyl ester 1676-81-9 C12H15NO5
Z-TYR-OME Z-TYR-OME 13512-31-7 C18H19NO5
5-AMINOVALERIC ACID 5-AMINOVALERIC ACID 660-88-8 C5H11NO2
N-Boc-N'-Fmoc-L-Lysine N-Boc-N'-Fmoc-L-Lysine 84624-27-1 C26H32N2O6
Boc-N-alpha-methyl-O-benzyl-L-tyrosine Boc-N-alpha-methyl-O-benzyl-L-tyrosine 64263-81-6 C22H27NO5
Fmoc-D-1-Naphthylalanine Fmoc-D-1-Naphthylalanine 138774-93-3 C28H23NO4
L-4,4'-BIPHENYLALANINE L-4,4'-BIPHENYLALANINE 155760-02-4 C15H15NO2
BOC-GLYCINE METHYL ESTER BOC-GLYCINE METHYL ESTER 31954-27-5 C8H15NO4
FMOC-L-4-CYANOPHENYLALANINE FMOC-L-4-CYANOPHENYLALANINE 173963-93-4 C25H20N2O4
N-(9-Fluorenylmethoxycarbonyloxy)succinimide N-(9-Fluorenylmethoxycarbonyloxy)succinimide 82911-69-1 C19H15NO5
4-(Trifluoromethyl)-DL-phenylglycine 4-(Trifluoromethyl)-DL-phenylglycine 142012-65-5 C9H8F3NO2
D-2-THIENYLALANINE D-2-THIENYLALANINE 62561-76-6 C7H9NO2S
FMOC-(R)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID 269398-78-9 C25H22N2O6
BOC-L-4-Trifluoromethylphe BOC-L-4-Trifluoromethylphe 114873-07-3 C15H18F3NO4
H-GLU(OET)-OH H-GLU(OET)-OH 1119-33-1 C7H13NO4
6-Aminonicotinic acid 6-Aminonicotinic acid 3167-49-5 C6H6N2O2
Fmoc-L-beta-homovaline Fmoc-L-beta-homovaline 172695-33-9 C21H23NO4
D-Tryptophan methyl ester hydrochloride D-Tryptophan methyl ester hydrochloride 14907-27-8 C12H15ClN2O2
DL-VALINE METHYL ESTER HYDROCHLORIDE DL-VALINE METHYL ESTER HYDROCHLORIDE 5619-05-6 C6H14ClNO2
FMOC-(S)-3-AMINO-4-(2-NAPHTHYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-NAPHTHYL)-BUTYRIC ACID 270063-40-6 C29H25NO4
GLYCYL-DL-LEUCINE GLYCYL-DL-LEUCINE 688-14-2 C8H16N2O3
N-(Benzyloxycarbonyloxy)succinimide N-(Benzyloxycarbonyloxy)succinimide 13139-17-8 C12H11NO5
Sermorelin Sermorelin 86168-78-7 C149H246N44O42S
D-2-Cyanophenylalanine D-2-Cyanophenylalanine 263396-41-4 C10H10N2O2
4-(4-Aminophenyl)butyric acid 4-(4-Aminophenyl)butyric acid 15118-60-2 C10H13NO2
BOC-D-2-THIENYLALANINE BOC-D-2-THIENYLALANINE 78452-55-8 C12H17NO4S
FMOC-L-3-Trifluoromethylphe FMOC-L-3-Trifluoromethylphe 205526-27-8 C25H20F3NO4
L-4-Pyridylalanine L-4-Pyridylalanine 37535-49-2 C8H10N2O2
BOC-D-4-THIAZOLYLALANINE BOC-D-4-THIAZOLYLALANINE 134107-69-0 C11H16N2O4S
3,3,3-Trifluoro-DL-alanine 3,3,3-Trifluoro-DL-alanine 17463-43-3 C3H4F3NO2
N-(tert-Butoxycarbonyl)-L-alanine N-(tert-Butoxycarbonyl)-L-alanine 15761-38-3 C8H15NO4
Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate 84793-24-8 C16H19NO5
BOC-L-2,4-DIAMINOBUTYRIC ACID(FMOC) BOC-L-2,4-DIAMINOBUTYRIC ACID(FMOC) 117106-21-5 C24H28N2O6
N-Ethyl-N-hydroxyethylaniline N-Ethyl-N-hydroxyethylaniline 92-50-2 C10H15NO
N-Boc-N'-benzyloxymethyl-L-histidine N-Boc-N'-benzyloxymethyl-L-histidine 79950-65-5 C19H25N3O5
BOC-D-TYR(BZL)-OH BOC-D-TYR(BZL)-OH 63769-58-4 C21H25NO5
Fmoc-D-proline Fmoc-D-proline 101555-62-8 C20H19NO4
Potassium L-aspartate Potassium L-aspartate 14007-45-5 C4H8KNO4
(2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline 64838-55-7 C11H17NO4S
FMOC-GLU-OALL FMOC-GLU-OALL 144120-54-7 C23H23NO6
L-5-Hydroxytryptophan L-5-Hydroxytryptophan 4350-09-8 C11H12N2O3
2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butanoic acid 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butanoic acid 73731-37-0 C19H19NO5
Alarelin Acetate Alarelin Acetate 79561-22-1 C58H82N16O14
3-Amino-4-methoxybenzoic acid 3-Amino-4-methoxybenzoic acid 2840-26-8 C8H9NO3
N-(tert-Butoxycarbonyl)glycylglycine N-(tert-Butoxycarbonyl)glycylglycine 31972-52-8 C9H16N2O5
(S)-2-Methylproline (S)-2-Methylproline 42856-71-3 C6H11NO2
BOC-D-2-FURYLALANINE DCHA SALT BOC-D-2-FURYLALANINE DCHA SALT 261380-18-1 C12H17NO5
N-Glycyl-L-leucine N-Glycyl-L-leucine 869-19-2 C8H16N2O3
BOC-(R)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID 190190-49-9 C19H23NO4
Fmoc-O-benzyl-L-tyrosine Fmoc-O-benzyl-L-tyrosine 71989-40-7 C31H27NO5
D-(-)-ALPHA-PHENYLGLYCINE ETHYL ESTER HYDROCHLORIDE D-(-)-ALPHA-PHENYLGLYCINE ETHYL ESTER HYDROCHLORIDE 17609-48-2 C10H14ClNO2
Trans-4-(Boc-amino)cyclohexanecarboxylic acid Trans-4-(Boc-amino)cyclohexanecarboxylic acid 53292-89-0 C12H21NO4
N-BOC-O-Benzyl-L-serine N-BOC-O-Benzyl-L-serine 23680-31-1 C15H21NO5
3-Methylamino-1,2-propanediol 3-Methylamino-1,2-propanediol 40137-22-2 C4H11NO2
3-(2-Naphthyl)-D-alanine 3-(2-Naphthyl)-D-alanine 76985-09-6 C13H13NO2
Acetylleucine Acetylleucine 99-15-0 C8H15NO3
FMOC-L-3-Methylphe FMOC-L-3-Methylphe 211637-74-0 C25H23NO4
QUISQUALIC ACID QUISQUALIC ACID 52809-07-1 C5H7N3O5
N-Cbz-L-glutamic acid N-Cbz-L-glutamic acid 1155-62-0 C13H15NO6
Melanotan II Melanotan II 121062-08-6 C50H69N15O9
DL-Histidine monohydrochloride monohydrate DL-Histidine monohydrochloride monohydrate 123333-71-1 C6H12ClN3O3
Z-PYR-OH Z-PYR-OH 32159-21-0 C13H13NO5
3-Methoxypropylamine 3-Methoxypropylamine 5332-73-0 C4H11NO
Boc-3-(3-pyridyl)-L-alanine Boc-3-(3-pyridyl)-L-alanine 117142-26-4 C13H18N2O4
BOC-(S)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID 270065-83-3 C16H20N2O4
N-Boc-N'-(9-xanthenyl)-L-glutamine N-Boc-N'-(9-xanthenyl)-L-glutamine 55260-24-7 C23H26N2O6
9-Fluorenemethanol 9-Fluorenemethanol 24324-17-2 C14H12O
Fmoc-Asp-OAll Fmoc-Asp-OAll 144120-53-6 C22H21NO6
N-BENZOYL-DL-ALANINE N-BENZOYL-DL-ALANINE 1205-02-3 C10H11NO3
L-Cysteine hydrochloride monohydrate L-Cysteine hydrochloride monohydrate 7048-04-6 C3H10ClNO3S
Nα-Boc-Nω-nitro-D-arginine Nα-Boc-Nω-nitro-D-arginine 50913-12-7 C11H21N5O6
N,N'-Di-tert-butoxycarbonyl-L-histidine N,N'-Di-tert-butoxycarbonyl-L-histidine 20866-46-0 C16H25N3O6
Dicyclohexylcarbodiimide Dicyclohexylcarbodiimide 538-75-0 C13H22N2
Boc-4-Bromo-L-beta-phenylalanine Boc-4-Bromo-L-beta-phenylalanine 261380-20-5 C14H18BrNO4
(R)-N-Boc-1-Naphthylalanine (R)-N-Boc-1-Naphthylalanine 76932-48-4 C18H21NO4
Boc-Dap-OH Boc-Dap-OH 73259-81-1 C8H16N2O4
4-ACETAMIDOANTIPYRINE 4-ACETAMIDOANTIPYRINE 83-15-8 C13H15N3O2
FMOC-LEU-OPFP FMOC-LEU-OPFP 86060-88-0 C27H22F5NO4
4-Amino-3-methylbenzoic acid 4-Amino-3-methylbenzoic acid 2486-70-6 C8H9NO2
N-BENZYL-L-PROLINE N-BENZYL-L-PROLINE 31795-93-4 C12H15NO2
3-AMINO-2-CHLOROBENZOIC ACID 3-AMINO-2-CHLOROBENZOIC ACID 108679-71-6 C7H6ClNO2
L-Alanine benzyl ester 4-toluenesulfonate L-Alanine benzyl ester 4-toluenesulfonate 42854-62-6 C17H21NO5S
1-Boc-3-piperidinecarboxylic acid 1-Boc-3-piperidinecarboxylic acid 84358-12-3 C11H19NO4
3-Amino-3-phenylpropionic acid 3-Amino-3-phenylpropionic acid 614-19-7 C9H11NO2
D(+)-Phenylalaninol D(+)-Phenylalaninol 5267-64-1 C9H13NO
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