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-L-BETA-HOMOSERINE(OTBU) FMOC-L-BETA-HOMOSERINE(OTBU) 203854-51-7 C23H27NO5
(R)-3-AMINO-4-(3-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(3-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE 269726-82-1 C11H12N2O2
FMOC-(S)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID 270063-38-2 C29H25NO4
N-(2,4-DINITROPHENYL)-L-LEUCINE N-(2,4-DINITROPHENYL)-L-LEUCINE 1655-57-8 C12H15N3O6
BOC-DAP(Z)-OH DCHA BOC-DAP(Z)-OH DCHA 65710-58-9 C28H45N3O6
4-(FMOC-AMINOMETHYL)BENZOIC ACID 4-(FMOC-AMINOMETHYL)BENZOIC ACID 164470-64-8 C23H19NO4
GLYCYL-L-SERINE GLYCYL-L-SERINE 7361-43-5 C5H10N2O4
H-D-PRO-OBZL HCL H-D-PRO-OBZL HCL 53843-90-6 C12H16ClNO2
(S)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID 275826-34-1 C9H10BrNO2
H-D-SER-OBZL HCL H-D-SER-OBZL HCL 151651-44-4 C10H14ClNO3
BOC-(R)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID BOC-(R)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID 190190-50-2 C21H25NO4
Fmoc-L-Glutamic acid gamma-methyl ester Fmoc-L-Glutamic acid gamma-methyl ester 145038-50-2 C21H21NO6
Boc-O-Benzyl-D-threoninol Boc-O-Benzyl-D-threoninol 168034-31-9 C16H25NO4
(S)-2-(Z-AMINO)-4-PHENYLBUTYRIC ACID (S)-2-(Z-AMINO)-4-PHENYLBUTYRIC ACID 127862-89-9 C18H19NO4
O-tert-Butyl-D-serine methyl ester hydrochloride O-tert-Butyl-D-serine methyl ester hydrochloride 78537-14-1 C8H18ClNO3
3-Chloro-L-alanine 3-Chloro-L-alanine 2731-73-9 C3H6ClNO2
L-beta-Homoproline hydrochloride L-beta-Homoproline hydrochloride 53912-85-9 C6H12ClNO2
H-CIS-HYP-OME HCL H-CIS-HYP-OME HCL 40126-30-5 C6H12ClNO3
FMOC-D-ALLO-ILE-OH FMOC-D-ALLO-ILE-OH 118904-37-3 C21H23NO4
BOC-N-ME-TYR-OH BOC-N-ME-TYR-OH 82038-34-4 C15H21NO5
ARG-GLY-ASP ARG-GLY-ASP 99896-85-2 C12H22N6O6
BZ-ALA-OH BZ-ALA-OH 2198-64-3 C10H11NO3
H-D-ARG-OME 2HCL H-D-ARG-OME 2HCL 78851-84-0 C7H18Cl2N4O2
BOC-(R)-3-AMINO-4-(3-METHYL-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3-METHYL-PHENYL)-BUTYRIC ACID 269398-83-6 C16H23NO4
H-THR-OTBU HCL H-THR-OTBU HCL 69320-90-7 C8H18ClNO3
D-DOPA D-DOPA 5796-17-8 C9H11NO4
D-BETA-HOMOSERINE D-BETA-HOMOSERINE 16504-57-7 C4H9NO3
D-HOMOPHENYLALANINE ETHYL ESTER HYDROC& D-HOMOPHENYLALANINE ETHYL ESTER HYDROC& 90940-54-8 C12H18ClNO2
FMOC-(S)-3-AMINO-4-(4-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(4-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 270065-81-1 C26H22F3NO4
Sarcosine methyl ester hydrochloride Sarcosine methyl ester hydrochloride 13515-93-0 C4H10ClNO2
AC-YVAD-AMC AC-YVAD-AMC 149231-65-2 C33H39N5O10
(S)-3-AMINO-4-(3-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE 270065-85-5 C11H12N2O2
N-(2,4-DINITROPHENYL)-DL-THREONINE N-(2,4-DINITROPHENYL)-DL-THREONINE 14401-07-1 C10H11N3O7
H-ALA-GLY-OH H-ALA-GLY-OH 687-69-4 C5H10N2O3
PHENYLTHIOHYDANTOIN-NORLEUCINE PHENYLTHIOHYDANTOIN-NORLEUCINE 4333-22-6 C13H16N2OS
Fmoc-D-Asp(OtBu)-OH Fmoc-D-Asp(OtBu)-OH 12883-39-3 C23H25NO6
2,6-Dimethyl-L-tyrosine 2,6-Dimethyl-L-tyrosine 123715-02-6 C11H15NO3
Copper Peptide Copper Peptide 49557-75-7 C14H24N6O4
AC-TRP-NH2 AC-TRP-NH2 2382-79-8 C13H15N3O2
Z-PHE-OSU Z-PHE-OSU 3397-32-8 C21H20N2O6
FMOC-(R)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID 269726-84-3 C26H22N2O4
DL-METHIONINOL DL-METHIONINOL 16720-80-2 C5H13NOS
Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate 118399-28-3 C12H13NO4
L-HOMOCYSTEINE L-HOMOCYSTEINE 6027-13-0 C4H9NO2S
FMOC-L-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID FMOC-L-1,2,3,4-TETRAHYDRONORHARMAN-3-CARBOXYLIC ACID 204322-23-6 C27H22N2O4
3-(N-Benzylamino)-L-alanine 3-(N-Benzylamino)-L-alanine 119830-32-9 C10H14N2O2
D-Styrylalanine D-Styrylalanine 264903-53-9 C11H13NO2
DL-ALPHA-(3-THIENYL)GLYCINE DL-ALPHA-(3-THIENYL)GLYCINE 38150-49-1 C6H7NO2S
FMOC-(R)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 269726-75-2 C26H22F3NO4
H-D-PRO-OTBU H-D-PRO-OTBU 90071-62-8 C9H17NO2
Boc-Phe-Phe-OH Boc-Phe-Phe-OH 13122-90-2 C23H28N2O5
BOC-DAP(Z)-OH BOC-DAP(Z)-OH 65710-57-8 C16H22N2O6
1-Pyrrolidinecarboxylicacid,3-(methylamino)-,1,1-dimethylethylester,(R)-(9CI) 1-Pyrrolidinecarboxylicacid,3-(methylamino)-,1,1-dimethylethylester,(R)-(9CI) 199336-83-9 C10H20N2O2
BOC-ASP(OBZL)-ONP BOC-ASP(OBZL)-ONP 26048-69-1 C22H24N2O8
L-Styrylalanine L-Styrylalanine 267650-37-3 C11H13NO2
N-ETHYLGLYCINE N-ETHYLGLYCINE 627-01-0 C4H9NO2
BOC-2-ABZ-OH BOC-2-ABZ-OH 68790-38-5 C12H15NO4
D-GLUTAMINE METHYL ESTER HYDROCHLORIDE D-GLUTAMINE METHYL ESTER HYDROCHLORIDE 74817-54-2 C6H13ClN2O3
FMOC-(S)-3-AMINO-4-(4-METHYL-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(4-METHYL-PHENYL)-BUTYRIC ACID 270062-97-0 C26H25NO4
GLYCYLGLYCINE HYDROCHLORIDE GLYCYLGLYCINE HYDROCHLORIDE 13059-60-4 C4H9ClN2O3
FMOC-(R)-3-AMINO-4-(2-METHYL-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(2-METHYL-PHENYL)-BUTYRIC ACID 269398-81-4 C26H25NO4
TYRPHOSTIN A25 TYRPHOSTIN A25 118409-58-8 C10H6N2O3
H-GLU(OALL)-OALL P-TOSYLATE H-GLU(OALL)-OALL P-TOSYLATE 20845-16-3 C18H25NO7S
 N-Methyl-L-proline N-Methyl-L-proline 475-11-6 C6H11NO2
S-2-Hydroxyethyl-L-cysteine S-2-Hydroxyethyl-L-cysteine 6367-98-2 C5H11NO3S
FMOC-D-LYS-OH HCL FMOC-D-LYS-OH HCL 201002-47-3 C21H25ClN2O4
N-BENZYLOXYCARBONYLGLYCINE THIOAMIDE N-BENZYLOXYCARBONYLGLYCINE THIOAMIDE 49548-40-5 C10H12N2O2S
BOC-(R)-3-AMINO-4-(3-THIENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3-THIENYL)-BUTYRIC ACID 269726-92-3 C13H19NO4S
(1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL 115651-77-9 C17H29NO
(R)- 3-Amino-5phenyl-pentanoic acid (R)- 3-Amino-5phenyl-pentanoic acid 147228-37-3 C11H15NO2
Brivanib alaninate Brivanib alaninate 649735-63-7 C22H24FN5O4
4-ACETAMIDOBUTYRIC ACID 4-ACETAMIDOBUTYRIC ACID 3025-96-5 C6H11NO3
DL-LEUCYL-GLYCYL-DL-PHENYLALANINE DL-LEUCYL-GLYCYL-DL-PHENYLALANINE 4294-25-1 C17H25N3O4
AG 825 AG 825 149092-50-2 C19H15N3O3S2
H-D-ALA-OET HCL H-D-ALA-OET HCL 6331-09-5 C5H12ClNO2
DL-ALANYL-GLYCYL-GLYCINE DL-ALANYL-GLYCYL-GLYCINE 927-21-9 C7H13N3O4
2-((4-Chloro-2-nitrophenyl)amino)ethanol 2-((4-Chloro-2-nitrophenyl)amino)ethanol 59320-13-7 C8H9ClN2O3
H-GLU(OBZL)-OBZL HCL H-GLU(OBZL)-OBZL HCL 4561-10-8 C19H22ClNO4
(-)-(1S,4R)-N-FMOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID (-)-(1S,4R)-N-FMOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID 220497-64-3 C21H19NO4
H-GLY-OIPR HCL H-GLY-OIPR HCL 14019-62-6 C5H12ClNO2
FMOC-(R)-3-AMINO-4-(4-METHYL-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(4-METHYL-PHENYL)-BUTYRIC ACID 269398-86-9 C26H25NO4
Fmoc-N-methyl-D-leucine Fmoc-N-methyl-D-leucine 103478-63-3 C22H25NO4
L-METHIONINE SULFOXIDE L-METHIONINE SULFOXIDE 3226-65-1 C5H11NO3S
PHE-GLY-GLY PHE-GLY-GLY 23576-42-3 C13H17N3O4
(2R,3S)-3-Phenylisoserine (2R,3S)-3-Phenylisoserine 136561-53-0 C9H11NO3
D-4-Hydroxyphenylglycine Methyl ester hydrochloride D-4-Hydroxyphenylglycine Methyl ester hydrochloride 57591-61-4 C9H12ClNO3
4-BORONO-D-PHENYLALANINE B10 ENRICHED 4-BORONO-D-PHENYLALANINE B10 ENRICHED 111821-49-9 C9H12BNO4
FMOC-CYS(STBU)-OH FMOC-CYS(STBU)-OH 73724-43-3 C22H25NO4S2
BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTYRIC ACID 270596-51-5 C15H20FNO4
FMOC-LYS(ME3)-OH HCL FMOC-LYS(ME3)-OH HCL 201004-29-7 C24H31ClN2O4
N-(2,4-DINITROPHENYL)-L-PHENYLALANINE N-(2,4-DINITROPHENYL)-L-PHENYLALANINE 1655-54-5 C15H13N3O6
(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-METHANOL 18881-17-9 C10H13NO
(S)-3-AMINO-4-(3,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 270063-50-8 C10H11Cl2NO2
DL-2-(4-CHLOROPHENYL)GLYCINE DL-2-(4-CHLOROPHENYL)GLYCINE 7292-70-8 C8H8ClNO2
H-D-GLU(OBZL)-OH H-D-GLU(OBZL)-OH 2578-33-8 C12H15NO4
DL-ALANYL-DL-METHIONINE DL-ALANYL-DL-METHIONINE 1999-43-5 C8H16N2O3S
3-AMINO-5-METHOXYCARBONYLPHENYLBORONIC ACID, HCL 3-AMINO-5-METHOXYCARBONYLPHENYLBORONIC ACID, HCL 380430-56-8 C8H10BNO4
BOC-(S)-3-AMINO-4-(2-FURYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(2-FURYL)-BUTYRIC ACID 270263-06-4 C13H19NO5
BOC-LYS(ALOC)-OH DCHA BOC-LYS(ALOC)-OH DCHA 110637-52-0 C27H49N3O6
3-AMINO-3-M-TOLYL-PROPIONIC ACID 3-AMINO-3-M-TOLYL-PROPIONIC ACID 68208-17-3 C10H13NO2
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