D-Homoproline - CAS 1723-00-8

D-Homoproline is a proline-based organocatalyst that has been investigated for several powerful asymmetric transformations, such as the Aldol, Mannich, and Michael reactions.

Product Information

Canonical SMILES
C1CCNC(C1)C(=O)O
InChI
InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m1/s1
InChI Key
HXEACLLIILLPRG-RXMQYKEDSA-N
Purity
≥ 99% (Assay)
MDL
MFCD00064346
Appearance
White to off-white crystalline powder
Storage
Store at 2-8 °C
Boiling Point
265.8 °C at 760 mmHg
Melting Point
272 °C(lit.)
Density
1.125 g/cm3
Optical Activity
27°(c=1 in water)
TSCA
No
WGK Germany
3

Safety Information

Signal Word
Warning
Precautionary Statement
P261 - P305+P351+P338
Hazard Statements
H315 - H319 - H335

Reference Reading

1.Improved Synthesis of the Unnatural Amino Acids AHMOD and AMD, Components of the Anticancer Peptaibol Culicinin D.
Ko KY1, Wagner S1, Yang SH1, Furkert DP1, Brimble MA1. J Org Chem. 2015 Sep 4;80(17):8631-6. doi: 10.1021/acs.joc.5b01265. Epub 2015 Aug 14.
An improved second-generation synthesis of the unnatural amino acid components of the anticancer peptaibol culicinin D has been developed. With a protected glutamic acid derivate as the starting material, the process readily delivered the Fmoc-protected free acid derivatives of AHMOD ((2S)-amino-(6R)-hydroxy-(4S)-methyl-8-oxodecanoic acid) and AMD ((2S)-amino-(4S)-methyldecanoic acid) required to support solid phase peptide synthesis (SPPS) for structure-activity studies of the natural product. The same approach also provides improved access to pipecolic acid derivatives. A novel Wittig reagent for one-carbon homologation of aldehydes, developed during this work, is also reported.
2.Novel Enzyme Family Found in Filamentous Fungi Catalyzing trans-4-Hydroxylation of l-Pipecolic Acid.
Hibi M1, Mori R2, Miyake R3, Kawabata H3, Kozono S1, Takahashi S1, Ogawa J4. Appl Environ Microbiol. 2016 Jan 22;82(7):2070-7. doi: 10.1128/AEM.03764-15.
Hydroxypipecolic acids are bioactive compounds widely distributed in nature and are valuable building blocks for the organic synthesis of pharmaceuticals. We have found a novel hydroxylating enzyme with activity toward l-pipecolic acid (l-Pip) in a filamentous fungus, Fusarium oxysporum c8D. The enzyme l-Pip trans-4-hydroxylase (Pip4H) of F. oxysporum (FoPip4H) belongs to the Fe(II)/α-ketoglutarate-dependent dioxygenase superfamily, catalyzes the regio- and stereoselective hydroxylation of l-Pip, and produces optically pure trans-4-hydroxy-l-pipecolic acid (trans-4-l-HyPip). Amino acid sequence analysis revealed several fungal enzymes homologous with FoPip4H, and five of these also had l-Pip trans-4-hydroxylation activity. In particular, the homologous Pip4H enzyme derived from Aspergillus nidulans FGSC A4 (AnPip4H) had a broader substrate specificity spectrum than other homologues and reacted with the l and d forms of various cyclic and aliphatic amino acids.
3.Investigations of the mechanism of the "proline effect" in tandem mass spectrometry experiments: the "pipecolic acid effect".
Raulfs MD1, Breci L, Bernier M, Hamdy OM, Janiga A, Wysocki V, Poutsma JC. J Am Soc Mass Spectrom. 2014 Oct;25(10):1705-15. doi: 10.1007/s13361-014-0953-5. Epub 2014 Jul 31.
The fragmentation behavior of a set of model peptides containing proline, its four-membered ring analog azetidine-2-carboxylic acid (Aze), its six-membered ring analog pipecolic acid (Pip), an acyclic secondary amine residue N-methyl-alanine (NMeA), and the D stereoisomers of Pro and Pip has been determined using collision-induced dissociation in ESI-tandem mass spectrometers. Experimental results for AAXAA, AVXLG, AAAXA, AGXGA, and AXPAA peptides are presented, where X represents Pro, Aze, Pip, or NMeA. Aze- and Pro-containing peptides fragment according to the well-established "proline effect" through selective cleavage of the amide bond N-terminal to the Aze/Pro residue to give yn (+) ions. In contrast, Pip- and NMA-fragment through a different mechanism, the "pipecolic acid effect," selectively at the amide bond C-terminal to the Pip/NMA residue to give bn (+) ions. Calculations of the relative basicities of various sites in model peptide molecules containing Aze, Pro, Pip, or NMeA indicate that whereas the "proline effect' can in part be rationalized by the increased basicity of the prolyl-amide site, the "pipecolic acid effect" cannot be justified through the basicity of the residue.
4.Pipecolic Acid Orchestrates Plant Systemic Acquired Resistance and Defense Priming via Salicylic Acid-Dependent and -Independent Pathways.
Bernsdorff F1, Döring AC1, Gruner K1, Schuck S1, Bräutigam A2, Zeier J3. Plant Cell. 2016 Jan;28(1):102-29. doi: 10.1105/tpc.15.00496. Epub 2015 Dec 15.
We investigated the relationships of the two immune-regulatory plant metabolites, salicylic acid (SA) and pipecolic acid (Pip), in the establishment of plant systemic acquired resistance (SAR), SAR-associated defense priming, and basal immunity. Using SA-deficient sid2, Pip-deficient ald1, and sid2 ald1 plants deficient in both SA and Pip, we show that SA and Pip act both independently from each other and synergistically in Arabidopsis thaliana basal immunity to Pseudomonas syringae. Transcriptome analyses reveal that SAR establishment in Arabidopsis is characterized by a strong transcriptional response systemically induced in the foliage that prepares plants for future pathogen attack by preactivating multiple stages of defense signaling and that SA accumulation upon SAR activation leads to the downregulation of photosynthesis and attenuated jasmonate responses systemically within the plant. Whereas systemic Pip elevations are indispensable for SAR and necessary for virtually the whole transcriptional SAR response, a moderate but significant SA-independent component of SAR activation and SAR gene expression is revealed.
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