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BOC-Amino Acids

Fmoc-His(Boc)-OH

CAS 81379-52-4
Catalog BAT-015021
Molecular Weight 477.51
Molecular Formula C26H27N3O6
Fmoc-His(Boc)-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

N-tert-Butyloxycarbonyl-S-(4-methylbenzyl)-D-penicillamine dicyclohexylamine

CAS 198474-61-2
Catalog BAT-015032
Molecular Weight 534.80
Molecular Formula C18H27NO4S.C12H23N
N-tert-Butyloxycarbonyl-S-(4-methylbenzyl)-D-penicillamine dicyclohexylamine

Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt

CAS 327156-92-3
Catalog BAT-015033
Molecular Weight 483.64
Molecular Formula C25H45N3O6
Boc-Dab(Alloc)-OH (dicyclohexylammonium) salt

N-Boc-1,6-hexanediamine

CAS 51857-17-1
Catalog BAT-015035
Molecular Weight 216.32
Molecular Formula C11H24N2O2
N-Boc-1,6-hexanediamine

N-Cbz-N'-BoC-L-ornithine

CAS 7733-29-1
Catalog BAT-015036
Molecular Weight 366.41
Molecular Formula C18H26N2O6
N-Cbz-N'-BoC-L-ornithine

Boc-L-His(Dnp)-OH

CAS 25024-53-7
Catalog BAT-015037
Molecular Weight 421.36
Molecular Formula C17H19N5O8
Boc-L-His(Dnp)-OH

3-(Boc-amino)pyrrolidine

CAS 99724-19-3
Catalog BAT-015045
Molecular Weight 186.25
Molecular Formula C9H18N2O2
3-(Boc-amino)pyrrolidine

N-Boc-1,3-propanediamine

CAS 75178-96-0
Catalog BAT-015047
Molecular Weight 174.24
Molecular Formula C8H18N2O2
N-Boc-1,3-propanediamine

N-Boc-cadaverine

CAS 51644-96-3
Catalog BAT-015056
Molecular Weight 202.29
Molecular Formula C10H22N2O2
N-Boc-cadaverine

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

Boc-N-Me-Tyr-OH

CAS 82038-34-4
Catalog BAT-015064
Molecular Weight 295.33
Molecular Formula C15H21NO5
Boc-N-Me-Tyr-OH

Boc-Lys-AMC

CAS 116883-12-6
Catalog BAT-015230
Molecular Weight 403.48
Molecular Formula C21H29N3O5
Boc-Lys-AMC

Boc-Dap-OtBu

CAS 77215-54-4
Catalog BAT-015351
Molecular Weight 260.33
Molecular Formula C12H24N2O4
Boc-Dap-OtBu

Boc-ε-azido-Nle-OH

CAS 846549-33-5
Catalog BAT-015383
Molecular Weight 272.31
Molecular Formula C11H20N4O4
Boc-ε-azido-Nle-OH

Boc-Cys(SEt)-OH · DCHA

CAS 25461-01-2
Catalog BAT-015424
Molecular Weight 462.72
Molecular Formula C10H19NO4S2 · C12H23N
Boc-Cys(SEt)-OH · DCHA

Fmoc-His(Boc)-OPfp

CAS 109053-20-5
Catalog BAT-015838
Molecular Weight 643.57
Molecular Formula C32H26F5N3O6
Fmoc-His(Boc)-OPfp

Boc-β,β-dimethyl-Cys(NPys)-OH

CAS 250375-03-2
Catalog BAT-015926
Molecular Weight 403.48
Molecular Formula C15H21N3O6S2
Sequence Boc-DL-Pen(Npys)-OH
Boc-β,β-dimethyl-Cys(NPys)-OH

Boc-Homoarg(Et)2-OH (symmetrical)

CAS 122532-94-9
Catalog BAT-015954
Molecular Weight 344.46
Molecular Formula C16H32N4O4
Boc-Homoarg(Et)2-OH (symmetrical)

Ethyl 3-(Boc-amino)-2,2-difluoropropanoate

CAS 847986-13-4
Catalog BAT-016015
Molecular Weight 253.24
Molecular Formula C10H17F2NO4
Ethyl 3-(Boc-amino)-2,2-difluoropropanoate

Introduction

In nature, there are 20 kinds of natural amino acids. In recent years, many efforts have been made in the modification of amino acids, and many non-natural amino acids have been created. Non-natural amino acids play an important role in the field of proteins and peptides. BOC-amino acid is a common and typical non-natural amino acid. There are many ways to synthesize BOC-amino acids. For example, tert-butyl oxycarbonyl (BOC) amino acids are commonly used as intermediates in the synthesis of polypeptides. The preparation method is the reaction of 1,1,3,3-tetramethylguanidinium salts of some amino acids with tert-butyloxycarbonyl azide in 4-dimethylaminopyridine as the solvent. Also, BOC group is used as a protecting group for amines in organic synthesis (Fig. 1).

Common amine protection and deprotection methods Fig. 1 Common amine protection and deprotection methods

Applications

Proteins: The programmed incorporation of unnatural amino acids with new functional side chains will provide a powerful approach for protein or even organism engineering with novel functionalities and capabilities. The recent successful development of technologies for incorporating unnatural amino acids into proteins in vivo has generated an additional strategy for modulating protein function. Unnatural amino acids can now be incorporated into a specific site of protein during translation by employing the amber codon as the genetic codon for unnatural amino acids. The incorporation of unnatural amino acids into proteins by site-specific mutagenesis provides a valuable new methodology for the generation of novel proteins that possess unique structural and functional features.

Synthesis of t-Boc-Met-CPT(1a) and the intermediate t-Bot-Gly-CPT(int 1) Fig. 2 Synthesis of t-Boc-Met-CPT(1a) and the intermediate t-Bot-Gly-CPT(int 1)

Peptide synthesis: The segment condensation method is an important technique in the synthesis of large peptides. Two different approaches are available, the minimum and the maximum protection strategies. Theoretically, the latter strategy is advantageous in t e r m of minimizing side reactions since all functional groups are protected during elongation reactions. If those protected segments can be assembled with Boc-amino acids, which are commonly used for the ordinary solid-phase method, the procedure should be more practical. Chemical peptide syntheses consume extremely large quantities of organic solvent due to the multiple solvent-based condensation steps,which damage the environment. Water-based peptide synthesis remained unexplored for a long period, because of the most common peptide building blocks, t-butyloxycarbonyl (BOC)- and 9-fluorenylmethoxycarbonyl (Fmoc)-amino acids , are sparingly soluble in water. aqueous peptide synthesis methods that utilize water-dispersible Boc- and Fmoc-amino acids nanoparticles. This technology uses suspended nanoparticle reactants for the coupling reaction to overcome the solubility problem and offers many advantages in terms of reaction efficiency Esters of N-tert-butoxycarbonyl (BOC) amino acids are widely used in peptide chemistry and in preparing several chiral auxiliaries such as β-amino alcohols, oxazolidinones, and α-amino aldehydes. N-Boc amino esters can be prepared either from amino esters by reacting with di-tert-butyl dicarbonate (diBoc), or from N-Boc amino acids by esterification. Both methods are unsatisfactory. In the first method, the reaction with diBoc requires alkaline conditions in which the ester group is not stable, although in some cases weaker bases can be used these require longer reaction times, and the yields are moderate. In the second method, commonly used esterification protocols involving reaction with an alcohol in the presence of acid catalysts such as HCl, H2SO4, thionyl chloride, PTSA, etc. cannot be used since the Boc group is unstable in acidic conditions.

Pesticide Biochemistry: Camptothecin, a quinolone alkaloid extracted from Camptotheca acuminata Decne, exhibits potential insecticidal activities against various insect species. The extensive applications of CPT on controlling pests have been prevented by its two major drawbacks. First, CPT has poor solubility in water and weak cuticular penetration. Second, the lactone ring of CPT is unstable which makes it easy transform to inactive carboxylate compound. introduction of t-Boc amino acids to 20-position on CPT improves contact assay and cytotoxicity of most derivatives toward Spodoptera exigua but reduces the inhibitory effect on relaxation activity of Spodoptera exigua topoisomerase I.

boc-amino-acids

References

  1. CHANKESHWARA S, CHAKRABORTI A. Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water[J]. Organic Letters, 2006, 8(15): 3259–62.
  2. PRASHAD M, HAR D, HU B, etc. Process Development of a Large-Scale Synthesis of TKA731:? A Tachykinin Receptor Antagonist[J]. Organic Process Research & Development, 2004, 8(3): 330–340.

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