16937-91-0

Basic information

• Product Name: H-D-ORN(Z)-OH
• Synonyms: D-ORNITHINE(Z)-OH;D-ORNITHINE(CBZ);H-D-ORN(Z)-OH;N-DELTA-CARBOBENZOXY-D-ORNITHINE;N-DELTA-CBZ-D-ORNITHINE;N-DELTA-Z-D-ORNITHINE;nδ-cbz-d-orinithine;N-Benzyloxycarbonyl-D-ornithine
• CAS NO: 16937-91-0
• Molecular Formula: C₁₃H₁₈N₂O₄
• Molecular Weight: 266.29
• Mol File: 16937-91-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 489.4 °C at 760 mmHg
• Flash Point: 249.8 °C
• Appearance: /
• Density: 1.234 g/cm³
• Storage Temp.: Store at RT.
• CAS DataBase Reference: H-D-ORN(Z)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-ORN(Z)-OH(16937-91-0)
• EPA Substance Registry System: H-D-ORN(Z)-OH(16937-91-0)

Safety Data

• Hazardous Substances Data: 16937-91-0(Hazardous Substances Data)

Usage

General Description

H-D-ORN(Z)-OH is a chemical compound also known as Z-D-Orn-OH. The "Z" in the name indicates a protecting group is present, which is used to stop certain reactions from occurring before it is removed in a later stage of the chemical synthesis. Specifically, it protects the amino acid ornithine during peptide synthesis. The "D" designation indicates that it is the dextrorotatory isomer of ornithine, meaning it rotates plane-polarized light to the right. H-D-ORN(Z)-OH is commonly used in pharmaceuticals and chemical research.

Upstream product

• 70671-55-5 For-D-Orn(Z)-OH 
• 2480-93-5 (R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine 
• 5874-56-6 For-DL-Orn(Z)-OH 
• 16682-12-5 D-ornithine hydrochloride 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 6205-08-9 N-acetylornithine 
• 2480-93-5 (R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine 
• 119027-79-1 L-β-benzyloxypropionyl-carbobenzoxyrnithine 
• 83160-02-5 N^α-p-toluenesulfonyl-N^δ-(benzyloxycarbonyl)-D-ornithine 
• 83160-09-2 (3S,6S,12R)-12-Amino-6-benzyl-3-isobutyl-1,4,7,10-tetraaza-cyclopentadecane-2,5,8,11-tetraone 
• 83160-08-1 N^α-Tos-D-Orn-Gly-Phe-Leu-OH 
• 16937-93-2 (R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-pentanoic acid 4-nitro-phenyl ester 
• 952729-12-3 (R)-Nδ-benzyloxycarbonyl-Nα-(9-fluorenylmethoxycarbonyl)ornithine 
• 1310327-11-7 (R)-Nδ-benzyloxycarbonyl-N-(4-ureidomethylbenzyl)ornithinamide hydrochloride 
• 191868-52-7 (R)-Nδ-benzyloxycarbonyl-Nα-(2,2-diphenylacetyl)-N-(4-ureidomethyl-benzyl)ornithinamide 
• 191855-71-7 (R)-Nα-(2,2-diphenylacetyl)-N-(4-ureidomethylbenzyl)ornithinamide 
• 13296-21-4 N^ε-(benzyloxycarbonyl)ornithine N-carboxyanhydride 
• 1093677-53-2 (R)-N'-(4-tert-butoxybenzyl)-N^α-(2,2-diphenylacetyl)ornithinamide 
• 1068148-44-6 (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide 

Relevant articles and documents

Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation

The preparation of peptide fragments containing dehydrovaline and dehydroisoleucine moieties present in the antibiotic myxovalargin is reported. Peptide formation is based on a copper-mediated C-N cross-coupling protocol between an acyl amide and a peptidic vinyl iodide. The presence of a neighboring arginine in the vinyl iodide posed a challenge with respect to the choice of the protecting group and the reaction conditions. It was found that ornithine - a suitable precursor - is better suited than arginine for achieving good yields for the C-N cross-coupling reaction. The optimized conditions were utilized for the synthesis of peptides 32, 33, 39 and 40 containing a neighboring ornithine as well as for the tripeptide 44 containing dehydroisoleucine with the correct stereochemistry.

Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers

(Chemical Equation Presented) Aqueous phosphoric acid (85 wt %) is an effective, environmentally benign reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. The reaction conditions are mild and offer good selectivity in the presence of other acid-sensitive groups, including CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers. The mildness of the reaction is further demonstrated in the synthesis of clarithromycin derivative 4, in which a tert-butyl ester is removed in the presence of cyclic carbamate, lactone, ketal, acetate ester, and epimerizable methyl ketone functionalities. The reaction preserves the stereochemical integrity of the substrates. The reactions are high yielding, and the workup is convenient.