73259-81-1

Basic information

• Product Name: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid
• Synonyms: Boc-Dapa-OH;Nα-Boc-L-2,3-diaminopropionic acid≥ 98% (HPLC);3-AMINO-(TERT-BUTOXYCARBONYL)-L-ALANINE;L-ALANINE, 3-AMINO-N-[(1,1-DIMETHYLETHOXY)CARBONYL]-;BOC-L-DAP-OH;BOC-L-DAPA-OH;BOC-L-2,3-DIAMINOPROPIONIC ACID;BOC-L-ALPHA,BETA-DIAMINOPROPIONIC ACID
• CAS NO: 73259-81-1
• Molecular Formula: C₈H₁₆N₂O₄
• Molecular Weight: 204.22
• EINECS: 1533716-785-6
• Product Categories: Amino Acids
• Mol File: 73259-81-1.mol

Chemical Properties

• Melting Point: 210 °C (dec.)
• Boiling Point: 364.4 °C at 760 mmHg
• Flash Point: 174.2 °C
• Appearance: white powder
• Density: 1.189 g/cm³
• Vapor Pressure: 2.64E-06mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly, Heated, Sonicated), Water (Sparingly, Heated, Sonicated)
• PKA: 2.88±0.16(Predicted)
• BRN: 4182136
• CAS DataBase Reference: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid(73259-81-1)
• EPA Substance Registry System: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid(73259-81-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 73259-81-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is used as a reactant for the solid phase synthesis of gramicidin S cyclic analogs, which possess antibiotic and hemolytic activities. These analogs are essential in the development of new antibiotics to combat drug-resistant bacteria and in the study of membrane permeability and ion channels.
N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is also used as a reactant in the synthesis of HCV protease inhibitor modified analogs. These analogs are vital in the development of antiviral drugs targeting Hepatitis C virus, a significant global health concern.
Used in Peptide Synthesis:
In the field of peptide synthesis, N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is used as a reactant for the solid phase synthesis of peptidic V1a receptor agonists. These agonists are crucial in the study and treatment of various physiological processes and disorders, including water and electrolyte balance, blood pressure regulation, and stress response.
N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is also used for directed peptide assembly at the lipid-water interface. This application is essential in the study of membrane proteins, their interactions, and the development of novel drug delivery systems and targeted therapies.

InChI:InChI=1/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m0/s1

Upstream product

• 98541-64-1 (2-Oxo-oxetan-3-yl)-carbamic acid tert-butyl ester 
• 98541-64-1 (2-Oxo-oxetan-3-yl)-carbamic acid tert-butyl ester 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 225780-77-8 2-(R)-(tert-butoxycarbonyl)-amino-3-azidopropionic acid 
• 7536-55-2 N-t-butyloxycarbonyl-D-asparagine 

Downstream Products

• 209223-73-4 (R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine 
• 252209-91-9 (R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine 
• 159652-30-9 (R)-2,3-bis-tert-butoxycarbonylaminopropionic acid 
• 1429555-43-0 C₂₃H₃₆N₄O₅ 
• 1429555-68-9 C₂₃H₄₂N₄O₅ 
• 81306-93-6 N²-tert-butoxycarbonyl-N³-benzyloxycarbonyl-D-2,3-diaminopropanoic acid 
• 61040-22-0 N^β-benzyloxycarbonyl-N^α-Boc-(R)-β-aminoalanine methyl ester 
• 1237004-93-1 N-(tert-butoxycarbonyl)-3-[(4-fluoro-2-nitrophenyl)amino]-D-alanine 
• 72071-28-4 (R)-2-tert-butoxycarbonylamino-3-(toluene-4-sulfonylamino)-propionic acid 
• 348081-41-4 (R)-2-tert-butoxycarbonylamino-3-(phenylmethanesulfonylamino)-propionic acid 
• 209223-32-5 (R)-(-)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid 
• 219325-44-7 benzoic acid 1-[2-(5-bromo-1H-indol-3-yl)-1-(9H-fluoren-9-ylmethoxycarbonyl)-ethylcarbamoyl]-2-{2-[2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-carbamoyl-propionylamino}-ethyl ester 
• 219325-45-8 Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester 
• 131570-56-4 (R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)propanoic acid 

Relevant articles and documents

High-efficiency preparation method of D-dencichine

The invention relates to a high-efficiency synthesis method of a hemostasis compound D-dencichine, comprising the following steps: firstly enabling D-serine to react with di-tert-butyl dicarbonate ester to generate Boc-D-serine, then generating Gabriel reaction with hydroxy of methylsulfonyl chloride activated Boc-D--serine to obtain N-alpha-Boc-D-alpha, beta-diaminopro, finally condensing with oxalate mono-methyl ester sylvite then performing hydrolytic acidification to obtain a dencichine crude product, and purifying to obtain a dencichine competitive product, with the product content reaching more than 99.8%. Compared with existing D-dencichine synthesis methods, the reaction condition is more mild, the operation is simple and convenient, the material cost is relatively low, and the hemostasis compound D-dencichine is environment-friendly, is suitable for industrial production, and solves the problem of resource for later development of clinical trial of D-dencichine.

New 2,3-diaminopropionic acid inhibitors of AGE and ALE formation

Novel 2,3-diaminopropionic acid-based molecules were synthesised and tested successfully as glyoxal/methylglyoxal scavengers and as AGE inhibitors. Addition of an 8-hydroxyquinoline moiety led to an increase of the overall activity. The compounds tested in this study were also proved to be efficient in trapping ALE precursor malondialdehyde. The Royal Society of Chemistry 2013.

Aminomethylene peptide nucleic acid (am -PNA): Synthesis, regio-/stereospecific DNA binding, and differential cell uptake of (α/γ, R / S) am- PNA analogues

Inherently chiral, cationic am-PNAs having pendant aminomethylene groups at α(R/S) or γ(S) sites on PNA backbone have been synthesized. The modified PNAs are shown to stabilize duplexes with complementary cDNA in a regio- and stereo-preferred manner with γ(S)-am PNA superior to α(R/S)-am PNAs and α(R)-am PNA better than the α(S) isomer. The enhanced stabilization of am-PNA:DNA duplexes is accompanied by a greater discrimination of mismatched bases. This seems to be a combined result of both electrostatic interactions and conformational preorganization of backbone favoring the cDNA binding. The am-PNAs are demonstrated to effectively traverse the cell membrane, localize in the nucleus of HeLa cells, and exhibit low toxicity to cells.

PNAs grafted with (α/γ, R/S)-aminomethylene pendants: Regio and stereo specific effects on DNA binding and improved cell uptake

PNAs grafted with cationic aminomethylene (am) pendants on the backbone at the glycyl (α) or ethylenediamine (γ) segments show regio (α/γ) and stereochemistry (R/S) dependent binding with complementary DNA. These are efficiently taken up by cells, with γ(S-am) aeg-PNA being the best in all properties.

Novel inhibitors of procollagen C-terminal proteinase. Part 1: Diamino acid hydroxamates

The parallel synthesis of novel inhibitors of procollagen C-terminal proteinase is described. The synthetic strategy allowed for the facile synthesis of a large number of side-chain diversified diamino acid hydroxamates, of which the D-diaminopropionic acid derivatives were shown to be single digit nanomolar PCP inhibitors.

The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: Rational modifications imparting PP1 selectivity

Based on the results from previously reported molecular modeling analyses of the interactions between the inhibitor microcystin and the serine-threonine protein phosphatases 1 and 2A, we have designed analogues of microcystin LA with structural modifications intended to impart PP1 selectivity. The synthesis of several first generation analogues followed by inhibition assays revealed that all three are PP1-selective, as predicted. Although the observed selectivities are modest, one of the designed analogues is more selective for PP1 than any known small molecule inhibitor. Copyright (C) 1999 Elsevier Science Ltd.

Studies related to the absolute configuration of cyclocinamide A: Total synthesis of 4(R),11(R)-cyclocinamide A

Coupling of the fluorenylmethyl ester 3 (R = Fm) of (S)-5- bromotryptophan with N(α)-BOC-(S)-asn-O-benzoyl-(R)-ise 9 gave rise to tripeptide 10. Cleavage of the BOC group in 10 followed by coupling with N(α)-BOC-N(β)-Fmoc-(R)-2,3-diaminopropanoic acid afforded tetrapeptide 11 which was transformed into cyclic peptide 12. Cleavage of the BOC in 12 followed by coupling with the glycine derived side chain 14 gave rise, after removal of the benzoyl group to 4(R),11(R)-cyclocinamide A(2) which was not identical to natural cyclocinamide A(1), suggesting that 1 possesses the 4(S),7(S),11(S),14(S) configuration.

Synthesis of [L-3-deoxymimosine4]-angiotensin I as an approach to the preparation of selective protein-tyrosine kinase (PTK) inhibitors

tert-Boc-L-3-Deoxymimosine (13) and tert-Boc-D-Deoxymimosine (16) were prepared in two steps from tert-Boc-L-asparagine and tert-Boc-D-asparagine, respectively. Both 13 and 16 were determined to be optically pure by derivatization with Marphey's reagent. Activation and coupling of 16 to L-isoleucine methyl ester resulted in a diastereomeric mixture of products containing 96% of the DL diastereomer and 4% of the LL diastereomer. [L-3-Deoxymimosine4]-angiotensin I was synthesized from 13 as an approach to the design and synthesis of selective protein-tyrosine kinase (PTK) inhibitors.

QUANTITATIVE SYNTHESIS OF L OR D N2-TERTBUTOXYCARBONYL-2,3-DIAMINOPROPANOIC ACID FROM PROTECTED L OR D SERINE-β-LACTONE

The reaction of ammonia on protected L or D serine-β-lactone was reinvestigated.An easy synthesis of N2-tertbutoxycarbonyl-L-2,3-diaminopropanoic acid (and D enantiomer), an important precursor of several antibiotics is proposed.