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D-Amino Acids

H-α-cyclopropyl-D-Ala-OH

CAS 1130070-43-7
Catalog BAT-014800
Molecular Weight 129.16
Molecular Formula C6H11NO2
H-α-cyclopropyl-D-Ala-OH

Fmoc-α-Me-D-Ser-lactone

CAS 1926163-89-4
Catalog BAT-014802
Molecular Weight 323.34
Molecular Formula C19H17NO4
Fmoc-α-Me-D-Ser-lactone

Fmoc-β-azido-D-Aib-OH BHA

CAS 1926163-91-8
Catalog BAT-014804
Molecular Weight 549.62
Molecular Formula C19H18N4O4.C13H13N
Fmoc-β-azido-D-Aib-OH BHA

Boc-D-Leu-OH

CAS 16937-99-8
Catalog BAT-015015
Molecular Weight 231.29
Molecular Formula C11H21NO4
Boc-D-Leu-OH

Fmoc-D-Pro-OH

CAS 101555-62-8
Catalog BAT-015020
Molecular Weight 337.37
Molecular Formula C20H19NO4
Fmoc-D-Pro-OH

H-D-Dap(Boc)-OMe

CAS 363191-25-7
Catalog BAT-015022
Molecular Weight 218.25
Molecular Formula C9H18N2O4
H-D-Dap(Boc)-OMe

Methyl D-valinate

CAS 21685-47-2
Catalog BAT-015026
Molecular Weight 131.17
Molecular Formula C6H13NO2
Methyl D-valinate

D-Homocysteine Lactone HCl

CAS 104347-13-9
Catalog BAT-015038
Molecular Weight 137.56
Molecular Formula C4H7NO2.HCl
D-Homocysteine Lactone HCl

D-Glutamic acid 1-tert-butyl ester

CAS 25456-76-2
Catalog BAT-015040
Molecular Weight 203.24
Molecular Formula C9H17NO4
D-Glutamic acid 1-tert-butyl ester

Fmoc-D-Asp-ODmb

CAS 200335-63-3
Catalog BAT-015043
Molecular Weight 505.53
Molecular Formula C28H27NO8
Fmoc-D-Asp-ODmb

N-Me-D-Phe-OH

CAS 56564-52-4
Catalog BAT-015052
Molecular Weight 179.22
Molecular Formula C10H13NO2
N-Me-D-Phe-OH

H-D-Gln(Trt)-OH

CAS 200625-76-9
Catalog BAT-015053
Molecular Weight 388.47
Molecular Formula C24H24N2O3
H-D-Gln(Trt)-OH

Boc-N-Me-D-Tyr-OH

CAS 178208-61-2
Catalog BAT-015063
Molecular Weight 295.33
Molecular Formula C15H21NO5
Boc-N-Me-D-Tyr-OH

BIBP 3226

CAS 159013-54-4
Catalog BAT-015241
Molecular Weight 473.57
Molecular Formula C27H31N5O3
BIBP 3226

N-Me-D-Phg-OH

CAS 30925-14-5
Catalog BAT-015272
Molecular Weight 165.19
Molecular Formula C9H11NO2
N-Me-D-Phg-OH

Ac-D-Arg-OH

CAS 2389-86-8
Catalog BAT-015295
Molecular Weight 216.24
Molecular Formula C8H16N4O3
Ac-D-Arg-OH

H-D-Abu-OtBu

CAS 313994-32-0
Catalog BAT-015312
Molecular Weight 159.23
Molecular Formula C8H17NO2
H-D-Abu-OtBu

Z-D-allo-Thr(tBu)-OH

CAS 100157-55-9
Catalog BAT-015325
Molecular Weight 309.36
Molecular Formula C16H23NO5
Z-D-allo-Thr(tBu)-OH

Etomidate

CAS 33125-97-2
Catalog BAT-015404
Molecular Weight 244.29
Molecular Formula C14H16N2O2
Etomidate

Etomidate Hydrochloride

CAS 53188-20-8
Catalog BAT-015405
Molecular Weight 280.75
Molecular Formula C14H17ClN2O2
Etomidate Hydrochloride

Introduction

Amino acids are the essential units of proteins, which is also one of the important nutrients of human life activities. Most amino acids contain asymmetric carbon atoms, with optical activity.

L-Amino Acid (Left) and D-Amino Acid (Right)Fig. 1. L-Amino Acid (Left) and D-Amino Acid (Right)

They mainly exist in the form of D-type and L-type isomers in nature and have different physiological functions in organisms. D-amino acids and its derivatives accounted for under about 10% of the total have been found. D-amino acids are present in high concentrations in microorganisms, plants, mammals, and humans and fulfill specific biological functions. Human beings can acquire D-amino acids through the ingestion of food, the derivation from endogenous microbial fora, liberation from metabolically unstable polypeptides, containing D-amino acids after racemization with aging, and through biosynthesis from L-amino acids. D-amino acids are often produced by chemical synthesis, fermentation, and enzymatic transformation. Chemical synthesis yields D-amino acids by chiral resolution of DL-amino acids or by asymmetric synthesis from chiral or prochiral starting materials. Due to the racemization of D-amino acids, high cost and low yields are the major disadvantages of chemical methods. Modified microorganisms without functional D-amino acid deaminases could be used for D-amino acid production, but because of complex enzyme systems and metabolic networks, it is difficult to achieve high optical purity and productivity. Enzymatic methods can yield D-amino acids with high optical purity, high productivity, and green process and are therefore ideal for the industrial manufacturing of D-amino acids.

Applications

Pharmaceutical industry: D-amino acids are incorporated or assimilated slower than the L-isomers, that the half-life of antibiotics and medicines containing D-amino acids is longer. D-amino acids are commonly used in semi-synthetic antibiotics synthesis, including traditional and new penicillin core and cephalosporin core antibiotics. For example, using D-Asp and amoxicillin as raw materials, aspoxicillin can be chemically synthesized . Aspoxicillin is popular due to its long half-life and low serum protein-binding characteristics. Compounds and peptides containing D-amino acids are very potent in disease therapy. Free D-amino acids are of great medicinal value. D-Phe alone can treat pain, depression, and Parkinson’s disease. D-Pro derivatives are often used for the treatment of diseases such as Alzheimer’s disease, diabetes mellitus, familial amyloid polyneuropathy, scrapie, and Kreuzfeld-Jacob disease.

Traditional and new core penicilin and cephalosporin semi-synthetic antibiotics containing D-AAsFig. 2. Traditional and new core penicilin and cephalosporin semi-synthetic antibiotics containing D-AAs(Gao et al., 2015)

Foods: Within the food industry, D-amino acids could be used for synthesizing intense sweeteners with higher potency than that lacking D-amino acids. Alitame, an L-Asp-D-Ala dipeptide sweetener, is about ten times more potent than Aspartame (LAsp-L-Phe dipeptide) . These sweeteners containing D-amino acids are not only highly potent but they also have low calorie. As such, they could be used in food products for people who suffer from diabetes. Besides, D-amino acids can also be used as food flavor agents, food additives, nutrition additives, and so on.

Cosmetics: D-amino acids could improve skin quality. D-Asp has both an antioxidant and collagen production-promoting effect. D-Glu can recover barriers and reduce wrinkle formation and skin roughness. D-Ser can reduce ultraviolet damage. Due to these effects on skin quality, D-amino acids of any type, as long as they were D-forms, have been added into an oil-in-water type emulsion skin cosmetics.

References:

  1. Zhang J, Xu Y, Li R (2013) Preparation method of aspoxicillin. China Patent 103333180Aa
  2. Heller B (1982) D-phenylalanine treatment. Unites States Patent 4355044
  3. Hertel C, Hoffmann T, Jakob-Roetne R, Norcross RD (2000) For treatment of diseases associated with amyloidosis, such as Alzheimer's disease, diabetes mellitus, familial amyloid polyneuropathy, scrapie, and kreuzfeld-jacob disease. United States Patent 6103910
  4. Walters DE (1995) Using models to understand and design sweeteners. J Chem Educ 72:680–683
  5. Grenby TH (1991) Intense sweeteners for the food industry: an overview. Trends Food Sci Technol 2:2–6
  6. Omura T, Furukawara T (2014) Oil-in-water type emulsion skin cosmetic. United States Patent 8607750B2
  7. Gao, X., Ma, Q., Zhu, H., 2015. Distribution, industrial applications, and enzymatic synthesis of D-amino acids. Applied Microbiology and Biotechnology 99, 3341–3349.

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