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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
FMOC-DL-7-AZATRYPTOPHAN FMOC-DL-7-AZATRYPTOPHAN C25H21N3O4
Ibuprofen lysinate Ibuprofen lysinate 57469-76-8 C19H32N2O4
N-(1-oxopropyl)-Glycine N-(1-oxopropyl)-Glycine 21709-90-0 C5H9NO3
N-BOC-3-CHLORO-D-TYROSINE
N-BOC-3-CHLORO-D-TYROSINE 478183-57-2 C14H18ClNO5
L-Lysine Diisocyanate L-Lysine Diisocyanate 45172-15-4 C10H14N2O4
1-(3-(TRIFLUOROMETHYL)BENZENESULFONYL)PROLINE 1-(3-(TRIFLUOROMETHYL)BENZENESULFONYL)PROLINE 251096-97-6 C12H12F3NO4S
Glycine, N-2-pyridinyl- (9CI) Glycine, N-2-pyridinyl- (9CI) 52946-88-0 C7H8N2O2
(s)-2-amino-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (s)-2-amino-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid 104974-45-0 C11H13NO2
(BIS-TERT-BUTOXYCARBONYLMETHYL-AMINO)-ACETIC ACID (BIS-TERT-BUTOXYCARBONYLMETHYL-AMINO)-ACETIC ACID 171557-31-6 C14H25NO6
FMOC-CYS(MTT)-OH FMOC-CYS(MTT)-OH 269067-38-1 C38H33NO4S
L-Proline, 4,4-difluoro-5-oxo-, methyl ester (9CI) L-Proline, 4,4-difluoro-5-oxo-, methyl ester (9CI) 333956-61-9 C6H7F2NO3
L-Arginine DL-Malate(1:1) L-Arginine DL-Malate(1:1)
Asp(OBzl)-OBzl HCl Asp(OBzl)-OBzl HCl C10H13NO2C7H8NO3S
3-thionaphthenylalanine 3-thionaphthenylalanine C11H11NO2S
D-Cysteine methyl ester hydrochloride D-Cysteine methyl ester hydrochloride C4H10ClNO2S
2,3,5-Trifluoro-L-phenylalanine 2,3,5-Trifluoro-L-phenylalanine 873429-59-5 C9H8F3NO2
l-Glutamic acid, N-coco acyl derivs., compds. with triethanolamine (1:1) l-Glutamic acid, N-coco acyl derivs., compds. with triethanolamine (1:1) 68187-29-1 C11H24N2O7
Fmoc-Glu-OtBu Fmoc-Glu-OtBu 4793-07-7 C24H27NO6
Fmoc-NH-PEG3-CH2COOH Fmoc-NH-PEG3-CH2COOH 139338-72-0 C23H27NO7
D-TRYPTOPHANOL OXALATE D-TRYPTOPHANOL OXALATE 58889-66-0 C13H16N2O5
N-(2-FUROYL)GLYCINE METHYL ESTER N-(2-FUROYL)GLYCINE METHYL ESTER 13290-00-1 C8H9NO4
AEROSOL 22 AEROSOL 22 38916-42-6 C26H48NNaO10S
BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID 151215-34-8 C10H16BrNO4
(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 364077-84-9 C10H15NO5
(ISOPROPYLAMINO)ACETIC ACID (ISOPROPYLAMINO)ACETIC ACID 3183-21-9 C5H11NO2
N-DODECANOYL-DL-HOMOSERINE LACTONE N-DODECANOYL-DL-HOMOSERINE LACTONE 18627-38-8 C16H29NO3
7-CHLORO-D-TRYPTOPHAN 7-CHLORO-D-TRYPTOPHAN 75102-74-8 C11H11ClN2O2
BOC-5-CHLORO-L-TRYPTOPHAN BOC-5-CHLORO-L-TRYPTOPHAN 114873-08-4 C16H19ClN2O4
H-ASN-OTBU H-ASN-OTBU 63094-81-5 C8H17ClN2O3
H-D-GLU(OBZL)-OTBU HCL H-D-GLU(OBZL)-OTBU HCL 90159-60-7 C16H24ClNO4
POLY-L-LEUCINE-1,3-DIAMINOPROPANE POLY-L-LEUCINE-1,3-DIAMINOPROPANE
N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER N,N-DIBENZYL-O-(T-BUTYLDIMETHYLSILYL)-L-SERINE METHYL ESTER 352530-50-8 C24H35NO3Si
FMOC-D-ABU-OH FMOC-D-ABU-OH 170642-27-0 C19H19NO4
GLYCINE THYMOL BLUE SODIUM SALT GLYCINE THYMOL BLUE SODIUM SALT C33H39N2NaO9S
(2R,3S)-3-PHENYLSERINE (2R,3S)-3-PHENYLSERINE 109120-55-0 C9H11NO3
Z-VAL-PHE-OME Z-VAL-PHE-OME 4817-95-2 C23H28N2O5
POLY-L-LYSINE HYDROCHLORIDE POLY-L-LYSINE HYDROCHLORIDE 26124-78-7 C6H15ClN2O2
Fmoc-L-HTyr(tBu)-OH Fmoc-L-HTyr(tBu)-OH 204384-69-0 C29H31NO5
POLY-L-LEUCINE-POLYETHYLENE GLYCOL MONOMETHYL ETHER POLY-L-LEUCINE-POLYETHYLENE GLYCOL MONOMETHYL ETHER
FMOC-D-ASP-OFM FMOC-D-ASP-OFM 214852-35-4 C33H27NO6
MESO-1 4-DIAMINO-2 3-BUTANEDIOL DIHYDROC MESO-1 4-DIAMINO-2 3-BUTANEDIOL DIHYDROC 20182-71-2 C4H12N2O2.2ClH
DL-BETA-HOMOMETHIONINE DL-BETA-HOMOMETHIONINE 158570-14-0 C6H13NO2S
L-Phenylalanine hydrochloride L-Phenylalanine hydrochloride 17585-69-2 C9H12ClNO2
4-AMINOBENZOIC ACID  SODIUM SALT 4-AMINOBENZOIC ACID SODIUM SALT 206557-08-6 H2NC6H4CO2NaxH2O
(R)-(+)-N-(TERT-BUTOXYCARBONYL)-O- (R)-(+)-N-(TERT-BUTOXYCARBONYL)-O- 152491-85-5 C14H31NO4Si
N-BOC-3-(3-METHYL-4-NITROBENZYL)-L- N-BOC-3-(3-METHYL-4-NITROBENZYL)-L- 114787-83-6 C20H26N4O6
L-(+)-CANAVANINE SULFATE MONOHYDRATE  9& L-(+)-CANAVANINE SULFATE MONOHYDRATE 9& 206996-57-8 C5H16N4O8S
(2S,3R)-3-METHYLGLUTAMIC ACID HYDROCHLORIDE SALT (2S,3R)-3-METHYLGLUTAMIC ACID HYDROCHLORIDE SALT 2445-97-8 C6H11NO4
5-HYDROXY-D-TRYPTOPHAN 5-HYDROXY-D-TRYPTOPHAN C11H12N2O3
2-[[(3-CHLOROPHENYL)SULFONYL]AMINO]-3-METHYLBUTANOIC ACID 2-[[(3-CHLOROPHENYL)SULFONYL]AMINO]-3-METHYLBUTANOIC ACID 1009549-57-8 C11H14ClNO4S
Z-TRP-OME Z-TRP-OME 2717-76-2 C20H20N2O4
3-AMINO-4-METHYLBENZYL ALCOHOL 3-AMINO-4-METHYLBENZYL ALCOHOL 81863-45-8 C8H11NO
(([3-(TRIFLUOROMETHYL)PHENYL]SULFONYL)AMINO)ACETIC ACID (([3-(TRIFLUOROMETHYL)PHENYL]SULFONYL)AMINO)ACETIC ACID 85845-02-9 C9H8F3NO4S
ethyl 4-amino-5-cyanosalicylate ethyl 4-amino-5-cyanosalicylate 72817-97-1 C10H10N2O3
D-Tryptophan, N-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl]- D-Tryptophan, N-[N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl]- 159634-94-3 C20H27N3O5
N-OCTANOYL-DL-HOMOSERINE LACTONE N-OCTANOYL-DL-HOMOSERINE LACTONE 106983-30-6 C12H21NO3
FMOC-ALLO-THR(TBU)-OH FMOC-ALLO-THR(TBU)-OH 201481-37-0 C23H27NO5
L-CYSTEINE (15N) L-CYSTEINE (15N) 204523-09-1 C3H7NO2S
N-(Phosphonomethyl)glycine diammonium salt N-(Phosphonomethyl)glycine diammonium salt 69254-40-6 C3H14N3O5P
D-Homophenylalanine  ethyl  ester D-Homophenylalanine ethyl ester 124044-66-2 C12H17NO2
(S)-2-AMINO-3-ETHOXY-PROPIONIC ACID HYDROCHLORIDE (S)-2-AMINO-3-ETHOXY-PROPIONIC ACID HYDROCHLORIDE 4775-82-0 C5H11NO3
BOC-5-FLUORO-L-TRYPTOPHAN BOC-5-FLUORO-L-TRYPTOPHAN 53478-53-8 C16H19FN2O4
N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER 155075-23-3 C14H17NO5
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-dimethyl ester N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-dimethyl ester 155405-81-5 C22H25N5O6
Valsartan n-Propyl Valsartan n-Propyl 952652-79-8 C23H27N5O3
L-Aspartic acid hydrochloride L-Aspartic acid hydrochloride 17585-59-0 C4H8ClNO4
N-ACETYL-S-(2-CYANOETHYL)-L-CYSTEINE N-ACETYL-S-(2-CYANOETHYL)-L-CYSTEINE 74514-75-3 C8H12N2O3S
BOC-LEU-OH·H2O BOC-LEU-OH·H2O 53296-34-7 C11H21NO4
CIS-2-AMINO-2-METHYLCYCLOPENTANECARBOXYLIC ACID HYDROCHLORIDE CIS-2-AMINO-2-METHYLCYCLOPENTANECARBOXYLIC ACID HYDROCHLORIDE 156292-34-1 C7H14ClNO2
N-ACETYL-D-ALA-D-ALA N-ACETYL-D-ALA-D-ALA 19993-26-1 C8H14N2O4
N-ETHYL-N-(HEPTADECAFLUOROOCTYL-SO2)GLYC IN K SALT,42 WT% IN H2O/2-BUTOXYETHANOL N-ETHYL-N-(HEPTADECAFLUOROOCTYL-SO2)GLYC IN K SALT,42 WT% IN H2O/2-BUTOXYETHANOL 2991-51-7 C12H9F17KNO4S
FMOC-GLYCINE  POLYMER-BOUND ON WANG FMOC-GLYCINE POLYMER-BOUND ON WANG 302912-51-2 C32H29NO5
N(ALPHA)  N-(IM)-DI-BOC-L-HISTIDINE N(ALPHA) N-(IM)-DI-BOC-L-HISTIDINE 17791-51-4 C17H27N3O6
METHYL N-ACETYLGLYCINATE METHYL N-ACETYLGLYCINATE 1117-77-7 C5H9NO3
P-AMINOBENZAMIDE GLYCINE P-AMINOBENZAMIDE GLYCINE C9H13N3O3
H-Orn(2-Cl-Z)-OH H-Orn(2-Cl-Z)-OH 118553-99-4 C13H17ClN2O4
DIEXO-3-AMINO-BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLIC ACID HYDROCHLORIDE DIEXO-3-AMINO-BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLIC ACID HYDROCHLORIDE 947601-81-2 C8H12ClNO2
H-ALLO-THR(TBU)-OH H-ALLO-THR(TBU)-OH 201353-89-1 C8H17NO3
FMOC-(R)-3-THIENYLGLYCINE FMOC-(R)-3-THIENYLGLYCINE C21H17NO4S
GHK GHK C14H24N6O4
L-Lysinol L-Lysinol C6H16N2O
D-Homocysteine D-Homocysteine C4H9NO2S
2,4-Dichloro-phenylalanine 2,4-Dichloro-phenylalanine C9H9Cl2NO2
α-amino-2-cyclopentenylacetic acid α-amino-2-cyclopentenylacetic acid C7H11NO2
3,5-Dichloro-L-tyrosine 3,5-Dichloro-L-tyrosine 15106-62-4 C9H9Cl2NO3
L-Cyclohexylglycine tert·butyl ester hydrochloride L-Cyclohexylglycine tert·butyl ester hydrochloride
DL-4-Thiazolylalanine DL-4-Thiazolylalanine 14717-97-6 C6H8N2O2S
(R)-3-Amino-3-(2-methyl-phenyl)-propionic acid (R)-3-Amino-3-(2-methyl-phenyl)-propionic acid 752198-38-2 C10H13NO2
Methyl N-Boc-L-proline-3-ene Methyl N-Boc-L-proline-3-ene 74844-93-2 C11H17NO4
Folic Acid-D4 Folic Acid-D4 171777-72-3 C19H15D4N7O6
H-SAR-OTBU HCL H-SAR-OTBU HCL 136088-69-2 C7H16ClNO2
7-chlorotryptophan 7-chlorotryptophan 153-97-9 C11H11ClN2O2
BOC-N-ME-DL-VAL-OH BOC-N-ME-DL-VAL-OH 13850-91-4 C11H21NO4
(2S)-2-amino-3-phenyl-propanoic acid (2S)-2-amino-3-phenyl-propanoic acid 67675-33-6 C9H11NO2
TSC AGAR TSC AGAR
H-CHA-OME HCL H-CHA-OME HCL 17193-39-4 C10H20ClNO2
BOC-3-(1-PYRENYL)-L-ALANINE BOC-3-(1-PYRENYL)-L-ALANINE 100442-89-5 C24H23NO4
TERT-BUTYL 4-HYDROXY-2-OXOPYRROLIDINE-1-CARBOXYLATE TERT-BUTYL 4-HYDROXY-2-OXOPYRROLIDINE-1-CARBOXYLATE 409341-03-3 C9H15NO4
L-Norvaline, 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-, 1,1-dimethylethylester L-Norvaline, 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-, 1,1-dimethylethylester 159877-09-5 C18H27NO7S
L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 1-1-methylethyl) ester L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 1-1-methylethyl) ester 88815-54-7 C16H21NO6
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