17121-19-6

Basic information

• Product Name: DD-DAP
• Synonyms: (2R,6R)-2,6-Diaminoheptanedioic acid;DD-DAP
• CAS NO: 17121-19-6
• Molecular Formula: C₇H₁₄N₂O₄
• Molecular Weight: 190.1971
• Mol File: 17121-19-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 426.7°Cat760mmHg
• Flash Point: 211.8°C
• Appearance: /
• Density: 1.344g/cm³
• CAS DataBase Reference: DD-DAP(CAS DataBase Reference)
• NIST Chemistry Reference: DD-DAP(17121-19-6)
• EPA Substance Registry System: DD-DAP(17121-19-6)

Safety Data

• Hazardous Substances Data: 17121-19-6(Hazardous Substances Data)

Upstream product

• 75650-93-0 L-2-amino-6-ketopimelate 
• 123-56-8 Succinimide 
• 3479-81-0 2,6-dibromo-heptanedioic acid 
• 1074-82-4 potassium phtalimide 
• 14289-34-0 (S,S)-2,6-diaminopimelic acid 
• 24277-38-1 (S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate 
• 102886-93-1 racem.-2,6-bis-benzyloxycarbonylamino-heptanedioic acid diamide 
• 354576-20-8 (6S,2R)-2,6-bis[(tert-butoxy)carbonylamino]-6-(methoxycarbonyl)hexanoic acid 
• 370860-88-1 methyl (2S,6R)-2,6-bis[(tert-butoxycarbonyl)amino]-7-hydroxyheptanoate 
• 370860-85-8 tert-butyl (4R)-4-{(3Z)-4-[(tert-butoxycarbonyl)amino]-5-methoxy-5-oxo-3-pentenyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 370860-87-0 tert-butyl (4R)-4-{(4S)-4-[(tert-butoxycarbonyl)amino]-5-methoxy-5-oxopentyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 135560-74-6 (3S,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 274694-68-7 (2S)-(-)-2-(p-toluenesulfonamido)-6-benzyloxy-hexanonitrile 
• 274694-67-6 (2S)-(+)-2-(p-toluenesulfinamido)-6-benzyloxy-hexanonitrile 

Downstream Products

• 59234-40-1 cis-meso-piperidine-2,6-dicarboxylic acid 
• 583-93-7 (2R,6S)-2,6-diaminoheptanedioic acid 
• 583-93-7 (2R,6R)-2,6-diaminoheptanedioic acid 
• 102886-93-1 racem.-2,6-bis-benzyloxycarbonylamino-heptanedioic acid diamide 
• 1198797-23-7 2,6-di([9H-fluoren-9-yl]methoxycarbonylamino)pimelic acid 
• 98469-29-5 C₁₇H₃₀N₂O₈ 
• 75650-93-0 L-α-amino-ε-ketopimelate 
• 56-87-1 L-lysine 
• 923-27-3 D-lysine 
• 1227363-67-8 C₃₃H₃₈N₂O₇ 
• 105541-49-9 C₂₁H₂₆N₂O₄ 
• 1227363-56-5 dibenzyl 2,6-bis((tert-butoxycarbonyl)amino)heptanedioate 
• 42920-79-6 meso-2,6-dibenzyloxycarbonylaminopimelic acid 
• 1269619-48-8 dibenzyl 2-amino-6-((tertbutoxycarbonyl)amino)heptanedioate 

Relevant articles and documents

A simple chromatographic route for the isolation of meso diaminopimelic acid

Meso diaminopimelic acid is an important noncoded amino acid found in Gram-negative bacterial peptidoglycan. In spite of its importance, this stereoisomer is not available commercially. A simple, economical procedure was developed for the isolation of pur

Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

A concise, stereoselective synthesis of meso-2,6-diaminopimelic acid (DAP)

The preparation of meso-2,6-diaminopimelic acid 1 is described. The key step in the synthesis is Suzuki coupling of the novel organoboron homoalanine equivalent 3 with methyl (2Z)-3-bromo-2-[(tert-butoxycarbonyl)amino]-2-propenoate 5.