N-β-Carbobenzoxy-L-α,β-diaminopropionic acid
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N-β-Carbobenzoxy-L-α,β-diaminopropionic acid

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Category
CBZ-Amino Acids
Catalog number
BAT-006947
CAS number
28415-54-5
Molecular Formula
C11H14N2O4
Molecular Weight
238.24
N-β-Carbobenzoxy-L-α,β-diaminopropionic acid
IUPAC Name
(2S)-2-amino-3-(phenylmethoxycarbonylamino)propanoic acid
Synonyms
H-Dap(Z)-OH
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H14N2O4/c12-9(10(14)15)6-13-11(16)17-7-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1
InChI Key
MUYNUUBAUQDGML-VIFPVBQESA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NCC(C(=O)O)N
1. Role of abscisic acid in modulating drought acclimation, agronomic characteristics and β-N-oxalyl-L-α,β-diaminopropionic acid (β-ODAP) accumulation in grass pea (Lathyrus sativus L.)
Hai-Yan Kong, Hao Zhu, Rui Zhou, Nudrat A Akram, Yi-Bo Wang, Cheng-Jing Jiao, You-Cai Xiong J Sci Food Agric. 2022 Apr;102(6):2553-2562. doi: 10.1002/jsfa.11597. Epub 2021 Nov 2.
Background: β-N-oxalyl-l-α,β-diaminopropionic acid (β-ODAP) is a physiological indicator in response to drying soil. However, how abscisic acid (ABA) modulates β-ODAP accumulation and its related agronomic characteristics in drought stressed grass pea (Lathyrus sativus L.) continue to be unclear. The present study aimed to evaluate the effects of ABA addition on drought tolerance, agronomic characteristics and β-ODAP content in grass pea under drought stress. Results: Exogenous ABA significantly promoted ABA levels by 19.3% and 18.3% under moderate and severe drought stress, respectively, compared to CK (without ABA, used as control check treatment). ABA addition activated earlier trigger of non-hydraulic root-sourced signal at 69.1% field capacity (FC) (65.5% FC in CK) and accordingly prolonged its operation period to 45.6% FC (49.0% FC in CK). This phenomenon was mechanically associated with the physiological mediation of ABA, where its addition significantly promoted the activities of leaf superoxide dismutase, catalase and peroxidase enzymes and the biosynthesis of leaf proline, simultaneously lowering the accumulation of malondialdehyde and hydrogen peroxide under moderate and severe stresses. Interestingly, ABA application significantly increased seed β-ODAP content by 21.7% and 21.3% under moderate and severe drought stress, but did not change leaf β-ODAP content. Furthermore, ABA application produced similar shoot biomass and grain yield as control groups. Conclusion: Exogenous ABA improved the drought adaptability of grass pea and promoted the synthesis of β-ODAP in seeds but not in leaves. Our findings provide novel insights into the agronomic role of ABA in relation to β-ODAP enrichment in grass pea subjected to drought stress. © 2021 Society of Chemical Industry.
2. β-N-oxalyl-L-α,β-diaminopropionic acid induces wound healing by stabilizing HIF-1α and modulating associated protein expression
Deepshikha Sharma, Preeti Singh, Surya S Singh Phytomedicine. 2018 May 15;44:9-19. doi: 10.1016/j.phymed.2018.04.024. Epub 2018 Apr 11.
Background: β-N-oxalyl-L-α,β-diaminopropionic acid (L-ODAP) is a non-protein amino acid with haemostatic property present in Lathyrus sativus. It is considered to be the causative agent of neurolathyrism that occurs upon prolonged overconsumption of Lathyrus sativus seeds. L-ODAP is used as a haemostatic drug in surgical dressings. We previously reported that it can stabilize hypoxia inducible factor (HIF)-1α in normoxic conditions. Hypothesis: We hypothesised that L-ODAP might affect wound healing by modulating cellular proliferation, migration and angiogenesis via HIF-1α stabilization. Study design: We performed in vitro assays to evaluate wound healing activity of L-ODAP. Further, we prepared pharmaceutical gel containing L-ODAP and checked its effect on healing of full thickness excision wounds using Wistar albino rats. Methods: Effect of L-ODAP on HT1080 cell line proliferation, migration and invasion was investigated. Further, gel containing L-ODAP was applied on full thickness excision wounds of Wistar rats. Western blot and zymography were performed with wound tissue extracts obtained 2 days post-wounding and histological and immunohistochemical analysis with regenerated tissue obtained 10 days post-wounding. Evaluation was made based on wound contraction percentage, histological analysis and protein expression levels. Results: L-ODAP significantly (P < 0.05) affected wound healing both in vitro and in vivo. At non-toxic concentrations, it induced cell proliferation, migration, invasion and MMP-2 & -9 expressions. L-ODAP treated wounds healed faster than vehicle treated ones. Significantly higher expression level of HIF-1α, VEGF-A, PDGF-A and matrix metalloproteases were observed in L-ODAP treated wounds. Conclusion: The present investigation explores potential of L-ODAP as a wound healing agent. L-ODAP positively affected wound healing both in vitro and in vivo and thus could be considered a natural wound healing agent.
3. β-N-oxalyl-L-α,β-diaminopropionic acid regulates mitogen-activated protein kinase signaling by down-regulation of phosphatidylethanolamine-binding protein 1
Nalini Jammulamadaka, Sandeepta Burgula, Rajesh Medisetty, Govindan Ilavazhagan, S L N Rao, Surya S Singh J Neurochem. 2011 Jul;118(2):176-86. doi: 10.1111/j.1471-4159.2011.07299.x. Epub 2011 Jun 2.
β-N-Oxalyl-L-α,β-diaminopropionic acid (l-ODAP) an α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptor agonist activates protein kinase C in white leghorn chick brain. The current study focuses on the protein kinase C downstream signaling targets associated with L-ODAP excitotoxicity in SK-N-MC human neuroblastoma cells and white leghorn male chick (Gallus domesticus) brain extracts. L-ODAP treatment in SK-N-MC cells (1.5 mM) and chicks (0.5 mg/g body weight) results in a decreased expression and increased phosphorylation of phosphatidylehthanolamine-binding protein 1 (PEBP1) up to 4 h which however, returns to normal by 8 h. D-ODAP, the non-toxic enantiomer however, did not affect PEBP1 levels in either chick brain or SK-N-MC cells. Decreased PEBP1 expression correlated with subsequent activation of Raf-1, MEK and ERK signaling components of the mitogen-activated protein kinase cascade and nuclear translocation of hypoxia inducible factor-1α (HIF-1α) in chick brain nuclear extracts and SK-N-MC cells. SK-N-MC cells over-expressing PEBP1 inhibited nuclear translocation of HIF-1α when treated with l-ODAP, indicating that down-regulation of PEBP1 is responsible for HIF-1α stabilization and nuclear localization. Excitotoxicity of L-ODAP may thus be the result of phosphorylation and down-regulation of PEBP1, a crucial signaling protein regulating diverse signaling cascades. L-ODAP induced convulsions and seizures in chicks could be the result of a hypoxic insult to brain.
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