Z-Dap-OH

Base Information

• Chemical Name: Z-Dap-OH
• CAS No.: 35761-26-3
• Molecular Formula: C11H14N2O4
• Molecular Weight: 238.243
• Hs Code.: 2924299090
• European Community (EC) Number: 689-800-4
• Nikkaji Number: J905.877J
• Mol file: 35761-26-3.mol

Synonyms:35761-26-3;Z-Dap-OH;(S)-3-Amino-2-(((benzyloxy)carbonyl)amino)propanoic acid;(S)-3-amino-2-(benzyloxycarbonylamino)propanoic acid;3-amino-2-N-Cbz-L-alanine;N-Carbobenzyloxy--amino-L-alanine;(S)-3-AMINO-2-(BENZYLOXYCARBONYLAMINO)-PROPANOIC ACID;(2S)-3-amino-2-(phenylmethoxycarbonylamino)propanoic acid;(2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoic acid;3-Amino-N-carbobenzoxy-L-alanine;3-AMINO-N-[(PHENYLMETHOXY)CARBONYL]-L-ALANINE;N-A-Cbz-L-2,3-diaminopropionic acid;(2S)-3-azaniumyl-2-(phenylmethoxycarbonylamino)propanoate;MFCD00237345;N-|A-Z-L-2,3-diaminopropionic acid;Z-Dpr-OH;n-alpha-cbz-l-2,3-diaminopropionic acid;3-Amino-N-Cbz-L-alanine;N-ALPHA-Z-L-2,3-DIAMINOPROPIONIC ACID;(s)-3-amino-2-benzyloxycarbonylaminopropanoic acid;(2S)-3-amino-2-benzyloxycarbonylaminopropionic acid;CBZ-L-BETA-AMINOALANINE;SCHEMBL2235427;Discontinued See: C176175;L-ALANINE, 3-AMINO-N-[(PHENYLMETHOXY)CARBONYL]-;FOXRXVSTFGNURG-VIFPVBQESA-N;3-Amino-N-(carbobenzoxy)-L-alanine;N?-Carbobenzyloxy-?-amino-L-alanine;AKOS007930035;AC-5657;CS-W002578;DS-0863;HY-W002578;2(S)-benzyloxycarbonylamino-beta-alanine;CBZ-L-2,3-DIAMINOPROPIONIC ACID;Z-Dap-OH, >=98.0% (NT);(S)-Nalpha-Cbz-2,3-diaminopropionic Acid;A6235;AM20040275;BB 0262194;N alpha -Carbobenzyloxy- beta -amino-L-alanine;Nalpha-(carbobenzyloxy)-beta-(amino)-L-alanine;3-amino-N-[(phenylmethoxy) carbonyl]-L-alanine;N?-Benzyloxycarbonyl-L-2,3-diamiopropionic Acid;Nalpha -(carbobenzyloxy)-beta-(amino)-L-alanine;(S)-3-Amino-2-(carbobenzoxyamino)propionic Acid;(S)-3-amino-2-benzyloxycarbonylaminopropionic acid;2(S)-benzyloxycarbonylamino-3-aminopropionic acid;2(S)-benzyloxycarbonylamino-3-aminopropionoic acid;3-Amino-2(S)-benzyloxycarbonylaminopropionic acid;(2S)-3-Amino-2-benzyloxycarbonylaminopropanoic acid;(s)-3-amino-2-benzyloxycarbonylamino-propionic acid;3-amino-2-(S)-benzyloxycarbonylamino-propionic acid;Nalpha -(benzyloxycarbonyl)-beta-(amino)-L-alanine;(2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propionic acid;(S)-3-amino-2-(((benzyloxy)carbonyl)amino) propanoic acid;(S)-2-(BENZYLOXYCARBONYLAMINO)-3-AMINOPROPIONIC ACID;N-alpha-Cbz-L-2,3-Diaminopropionic acid;Nalpha-Carbobenzyloxy-beta-amino-L-alanine;3-AMINO-2-N-CBZ-L-ALANINE

Chemical Property of Z-Dap-OH

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 2.18E-09mmHg at 25°C
• Melting Point: 240oC (dec.)
• Refractive Index: 1.571
• Boiling Point: 463.8 °C at 760 mmHg
• PKA: 2.86±0.16(Predicted)
• Flash Point: 234.3 °C
• PSA: 101.65000
• Density: 1.303 g/cm³
• LogP: 1.41590
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: Soluble in dilute acid.
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 238.09535693
• Heavy Atom Count: 17
• Complexity: 264

Purity/Quality:

99% ^*data from raw suppliers

Na-Carbobenzyloxy-b-amino-L-alanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CN)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CN)C(=O)O
• Uses: Nalpha-Benzyloxycarbonyl-L-2,3-diaminopropionic acid is a important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins. Important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins

Technology Process of Z-Dap-OH

There total 14 articles about Z-Dap-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

N-benzyloxycarbonyl-L-asparagine (2304-96-3) → (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In water; ethyl acetate; acetonitrile; at 20 ℃; for 4h;

DOI:10.1055/s-2008-1042756

Reference yield: 92.0%

N2-benzyloxycarbonyl-N3-(p-methoxybenzyloxycarbonyl)-L-2,3-diaminopropanoic acid (81659-77-0) → (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 3h;

DOI:10.1246/bcsj.55.633

Reference yield: 54.3%

(S)-2,3-diaminopropanoic acid hydrochloride (1482-97-9) + benzyl chloroformate (501-53-1,94274-21-2) → Nβ-(benzyloxycarbonyl)-L-α,β-diaminopropionic acid (28415-54-5) + (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3)

Guidance literature:

With sodium hydroxide; In toluene; for 4.5h; 0.05 M phosphate buffer (pH 7);

DOI:10.1021/jm00137a015

upstream raw materials:

L-carbobenzyloxy-β-chloroalanine

N-benzyloxycarbonyl-L-serine methyl ester

N-benzyloxycarbonyl-L-asparagine

((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester

Downstream raw materials:

N₂-Z-N₃-propynoylamino-L-alanine

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

ethyl (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

Nα-CBz-β-acetylamino-L-alanine

Refernces

• 1、 Chen, Yue,Cui, Yingjun,Deng, Yangping,Fu, Qiang,Jiang, Peng,Li, Jing,Lin, Jianping,Liu, Yang,Meng, Qing,Sun, Yuanjun,Wang, Liang,Wang, Mukuo,Xu, Honglei,Ye, Baijun,Zhang, Mengyi,Zhang, Songming,Zhang, Tingrong,Zhao, Xiuhe. "Elastase Inhibitor Cyclotheonellazole A: Total Synthesis and in Vivo Biological Evaluation for Acute Lung Injury". . . Retrieved 2022/01/27.
• 2、 -. "Antibody-drug conjugate with acidic self-stabilizing joint". Paragraph 0113; 0114; 0115; 0116. . Retrieved 2018/09/14.