Synonym
Streptobiosamine;
IUPAC/Chemical Name
(2R,3R)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxy-2-((S)-1-hydroxyethyl)succinaldehyde
InChi Key
UNTJYOFZBHSHIU-HXYRURAXSA-N
InChi Code
InChI=1S/C13H23NO9/c1-6(18)13(21,5-17)8(4-16)23-12-9(14-2)11(20)10(19)7(3-15)22-12/h4-12,14-15,18-21H,3H2,1-2H3/t6-,7-,8-,9-,10-,11-,12-,13+/m0/s1
SMILES Code
O=C[C@@H]([C@]([C@H](C)O)(C=O)O)O[C@H]1[C@@H](NC)[C@@H]([C@H]([C@H](CO)O1)O)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
337.32
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: FRIED J, WINTERSTEINER O. Streptomycin; reduction and oxidation products of streptomycin and of streptobiosamine. J Am Chem Soc. 1947 Jan;69(1):79-86. PubMed PMID: 20291044.
2: KUEHL FA Jr, FLYNN EH, et al. Streptomyces antibiotics; the structure of streptobiosamine. J Am Chem Soc. 1946 Dec;68(12):2679-84. PubMed PMID: 20282405.
3: FRIED J, WALZ DE, WINTERSTEINER O. Streptomycin; 4-desoxy-L-erythrose (threose) phenylosazone from streptobiosamine. J Am Chem Soc. 1946 Dec;68(12):2746. PubMed PMID: 20282418.
4: KUEHL FA Jr, PECK RL, et al. Streptomyces antibiotics; the position of the linkage of streptobiosamine to streptidine in streptomycin. J Am Chem Soc. 1947 May;69(5):1234. PubMed PMID: 20240531.
5: Brink NG, Kuehl FA Jr, Folkers K. STREPTOMYCES ANTIBIOTICS. III. DEGRADATION OF STREPTOMYCIN TO STREPTOBIOSAMINE DERIVATIVES. Science. 1945 Nov 16;102(2655):506-7. PubMed PMID: 17750721.
6: CARTER HE, LOO YH, SKELL PS. Streptomycin; the linkage between streptidine and streptobiosamine. J Biol Chem. 1947 Apr;168(1):401. PubMed PMID: 20291104.
7: FRIED J, STAVELY HE. Streptomycin; degradation of streptomycin B to streptidine, streptobiosamine and d-mannose. J Am Chem Soc. 1947 Jun;69(6):1549. PubMed PMID: 20343921.
8: KUEHL FA Jr, CLARK RL, et al. Streptomyces antibiotics; configuration of streptose and streptobiosamine. J Am Chem Soc. 1949 Apr;71(4):1445-8. PubMed PMID: 18128367.
9: KUEHL FA Jr, BISHOP MN, et al. Streptomyces antibiotics; dihydrostreptosonic acid lactone and configuration of streptose and streptobiosamine. J Am Chem Soc. 1948 Jul;70(7):2613. PubMed PMID: 18875135.
10: Krasil'nikov OL, Anisova LN, Khokhlov AS. [Actinomyces streptomycini mutants blocked in the biosynthesis of the streptobiosamine portion of the streptomycin molecule]. Antibiotiki. 1978 Feb;23(2):135-8. Russian. PubMed PMID: 629525.
11: Harwood JH, Smith DH. Resistance factor-mediated streptomycin resistance. J Bacteriol. 1969 Mar;97(3):1262-71. PubMed PMID: 4887506; PubMed Central PMCID: PMC249843.
12: MAJUMDAR SK, KUTZNER HJ. Myo-inositol in the biosynthesis of streptomycin by Streptomyces griseus. Science. 1962 Mar 2;135(3505):734. PubMed PMID: 14468644.
13: STAVELY HE, WINTERSTEINER O, et al. Streptomycin; some derivatives and reactions of dihydrostreptobiosamine. J Am Chem Soc. 1947 Nov;69(11):2742-7. PubMed PMID: 20270823.
14: BRINK NG, KUEHL FA Jr, et al. Streptomyces antibiotics; the structure of tetraacetylbisdesoxystreptobiosamine. J Am Chem Soc. 1946 Nov;68(11):2405. PubMed PMID: 21065318.
15: Krasil'nikova OL, Anisova LN, Khokhlov AS. [Interaction of streptidin-dependent Actinomyces streptomycini (Streptomyces griseus) mutants No. 170 and 145 with mutants having blocks at various stages of streptomycin biosynthesis]. Antibiotiki. 1978 Apr;23(4):308-13. Russian. PubMed PMID: 417668.
