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Bio-Synthesis offers oligo synthesis using degenerate base modification. Degenerate bases, wobble bases or mixed bases, can be introduced at any positiion in an oligomer sequences. Degenerate base modifications of a primer provide more flexibility in their specificity where degenerate primer are used to amplfy DNA in situations where only the protein sequence of a gene is known , or where sequence from one species is the basis for the amplication of a homologous region or gene in another species.

Serveral methods of degenerate site enhanced oligo primer synthesis offered at Bio-Synthesis. We offered mixed base of different combination of A/C/G/T, trimer codon incorporation , non-natural base P and K or universal bases( 3- intropyrrole, 5-nitroindole, or inosine ). These degenerate universal base analogs can replace any of the four DNA bases without base pairing bias or destabilizing base-pair interactions.Contact Bio-Synthesis for degenrate base modifications.

Incorporation of degenerate base modifications is desirable in cases when either imprecise or random base-pairing is required, and the resulting “mis-matched” complements need to be stable. Application of using degenerate base includes:

  • Reverse-translation of known protein sequence
  • Development of an in vitro or in vivo probe to hybridize to related but distinct gene
  • In viro site-direct mutagenesis and motif cloning.
Mixed Bases (N)

There are three strategies can be use for primer design to dealt with the degeneracy of the genetic code. First, a mixed base addition (N) is used to form the degenerate site. This approach is best if the number of degenerate sites is small.

Universal Bases

Second option is the use of 2’-deoxyInosine, Inosine, or Nebularine or 2’-deoxyNebularine which is capable of pairing with all four natural nucleotides with unequal affinity (I-C >I-A>I-T~I-G>I-I). Regardless, inosine continues to be successfully used in a variety of applications which require degeneracy at certain base positions of primers and probes , particularly at wobble positions, where degeneracy might be needed to permit annealing to many different, but closely related sequences.

Incorporating inosine instead of mixed bases in the degenerate PCR reaction often yields superior amplification results due toinefficient hybridization of the mixed-base degenerate primers. When a guanine-rich PCR primer is needed, substitution of inosine for one or more guanines helps reduce undesirable G-quartet formation and primer-dimer artifacts . For DNA microarrays, inosine can be used to increase the stability of an oligo library without increasing the library’ s diversity, at considerable cost savings .

The third option is the use of a universal nucleoside. In this strategy, the base analog does not hybridize significantly to the other four bases and makes up some of the duplex destabilization by acting as an intercalating agent. 5-nitroindole base-pairs indiscriminately with any of the natural nucleotides, a consequence of the fact that it interacts via base-stacking, not hydrogen bonding . 5-nitroindole has been incorporated into nested sets of oligo probes to target regions of rRNA in different microorganisms in order to ensure equal probe specificity across them . However, its ability to act as a “universal” degenerate base is position-dependent, that is, on where it is located within a primer or probe. Other degenerate bases, such as 2-amino purine, iso-dG, and 5-methyliso-dC, can be use as degenerate base.

Rules for the design of primers containig Universal Bases:
  1. Substitution of universal bases is less destabilizing towards the termini of oligonucleotides than towards the center.
  2. Grouped substitution s are more easily tolerated than spaced, i.e. contiguous rather than codon third substitutions
  3. More than 2-3 codon their substitutions in a 20 mer may not realiably yield a sequencing ladder or a PCR product .
  4. More than a 3 contigous substitutions in a primer may give reduced PCR products or an incorrect sequencing ladder.
  5. 3'-substitutions may lead to incorrect PCR amplification or failure to give a proper sequencing ladder.
Degenerate Bases: P and K

Some primer/template systems may be unable to tolerate the level of destabilization caused by universal base. Such systems may then be candidates for the use of primers containing P and K degenerate bases. While inosine has functioned relatively well in its role as a universal base but its hybridization properties are not ideal and, when incorporated into PCR primers, it has been reported to code primarily as G. 5-nitroidole and 3-nitropyrrole are categoriezed to the same group of universal bases but their destabilizing effect on duplexes makes them suitable for use in PCR primers with only a few substitution sites. Fully degenerate sites may be formed in an oligonucleotide using an A/C/G/T mix but the complexity of the mixture of oligonucleotides formed in this way obviously rises with each insertion and limits the usefulness of this technique. The use of K-2'-deoxyribose or P-2'-deoxyribose are degenerate bases mimicking a C/T and A/G mix can be used to replace the natural DNA bases with little estabilzation, and it has been shown that they can be substituted independently into oligonucleotide primers for the polymerase chain reaction. They can also be used together in the oligomers to prime DNA syntehsis in PCR and in sequencing reactions more effective than dI.

References:
  1. R. Nichols, P.C. Andrews, P. Zhang, and D.E. Bergstrom, Nature, 1994, 369, 492-493.
  2. D.E. Bergstrom, P. Zhang, P.H. Toma, P.C. Andrews, and R. Nichols, J. Am. Chem. Soc., 1995, 117, 1201-1209.
  3. D. Loakes and D.M. Brown, Nucleic Acids Res., 1994, 22, 4039-4043.
  4. D. Loakes, D.M. Brown, S. Linde, and F. Hill, Nucleic Acids Res., 1995, In press.
  5. P. Kong Thoo Lin and D.M. Brown, Nucleic Acids Res., 1992, 20, 5149-5152.
  6. P. Kong Thoo Lin and D.M. Brown, Nucleic Acids Res., 1989, 17, 10383.
  7. D.M. Brown and P. Kong Thoo Lin, Carbohydrate Research, 1991, 216, 129-139.

Bio-Synthesis degenerate site modification can be incorporate at any position of an oligonucleotide . Every oligo synthesized is strictly controlled for quality by using either MALDI-TOF mass spectrometry or polyacrylamide gel electrophoresis (PAGE) analysis. Final yields are determined using UV absorbance at OD260 In addition, we perform QC methods tailored to specific modifications, such as OD ratio measurement where appropriate.

For additional information, please Contact us.

Inosine (rI)

Inosine the most commonly used degereated modified base which more or less is a universal base. It can be incorporate at 5', internal and 3' end of the oligonucleotide. More about 3' Deoxyadenosine Oligo Modification

  • Modification Code: rI, rInoisine
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y
  • Molecular Weight (mw) 331
  • Extinction Coefficient (ec) 7.5

More about Inosine (rI) Oligo Modification

2'-DeoxyInosine (dI)

2'-deoxy inosine (dI, dInosine) Inosine the most commonly used degereated base or univeral base. It has the ability to base pair unbiasely with each of the four standard A,C,G and T bases. 2'-deoxyInosine can be place at 5', internal and 3' end of the oligomers. It is often placed in ambiguous positions in degenerate amino acid codoens of custom synthesized oligos.

  • Modification Code: dI, dInosine
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y
  • Molecular Weight (mw) 314
  • Extinction Coefficient (ec) 7.5

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2'-Deoxynebularine Purine (dNeb)

2'-deoxynebularine, dNeb is a universal base analogue. It lacks exocyclic functional groups and offers an altered hydrogen bonding 'base pairs' with each of the natural DNA/RNA bases while retaining base stacking ability. 2'-deoxyINebularine can be place at 5', internal and 3' end of the oligomers. It is often placed in ambiguous positions in degenerate amino acid codoens of custom synthesized oligos.

  • Modification Code: dNeb
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

More about 2'-Deoxynebularine (dNeb) Oligo Modification

Nebularine Purine Riboside (rNeb)

Nebularine, rNeb, is a ribo adenosine analog that lacks exocyclic functional groups and offers an altered hydrogen bonding scheme while retaining base stacking ability. Nebularine can be place at 5', internal and 3' end of the oligomers.

  • Modification Code: rNeb
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

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2'-O-Methylinosine (2OMe-I)

2'-O-Methylinosine, 2OMe-I is a universal base analogue. It can 'base pairs' with each of the natural RNA bases while retaining base stacking ability. 2'-OMethyl Inosine can be place at 5', internal and 3' end of the oligomers. It is often placed in ambiguous positions in degenerate amino acid codoens of custom synthesized oligos.

  • Modification Code: 2OMe-I
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

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2-Amino Purine (2dAP)

2'-Amino Purine, 2dAP is a adenine and guanine analog. It can 'base pairs' with thymine and cytosine without significantly affect duplex stability. It is an attractive choice for use as a probe in nucleic acid secondary structural studies, both because its fluorescence is highly sensitive to the nature of the local environment. 2-Amino purine (2dAP) can be use to substitute for dA and dG, it has been used to characterize the effects of DNA mismatch repair on mutagenesis.

  • Modification Code: 2dAP
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

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2-Amino Purine Riboside (2rAP)

2'-Amino Purine, 2rAP is a riboside adenine and guanine analog. It can 'base pairs' with thymine and cytosine without significantly affect duplex stability. It is an attractive choice for use as a probe in nucleic acid secondary structural studies, both because its fluorescence is highly sensitive to the nature of the local environment. 2-Amino purine riboside (2rAP) can be use to substitute for rA and rG, it has been used to characterize the effects of RNA mismatch repair on mutagenesis.

  • Modification Code: 2rAP
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

More about 2-Amino Purine (2rAP) Oligo Modification

5-Methyl Iso-deoxycytosine (5Me-Iso-dC)

5-Methyl iso-deoxycytosine, 5-Me-iso-dC forms a Watson-Crick base pair with iso-dG. Substitution of a 5-Me-iso-dC:iso-dG base pair for a C:G pair increases the Tm of the resulting duplex by ~2degC per base pair substitution, Furthermore, since 5-Me-iso-dC does not pair with dG, 5-Me-iso-dC:iso-dG can function as a stable unnatural base pair that can be used to expand the genetic code.

  • Modification Code: 5-Me-Iso-dC
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y
  • Molecular Weight (mw) 303.21
  • Extinction Coefficient (ec) 5.3

More about 5-Methyl Iso-dC Oligo Modification

5-Nitroindole (5N-indole)

5-Nitroindole can be use as a universal base analog in oligonucleotide. This aromatic compound does not discriminate between the four natural nucleotide bases in duplex formation. In contrast to deoxyinosine (dI), which often used as a “universal” base with fairly strong base-pair bias. 5-Nitroindole’s lack of discrimination (“universality”) is a consequence of the fact that it doesn’t form hydrogen bonds with natural bases. Instead, 5-nitroindole stabilizes the duplex via base-stacking interactions. Much research on 5-nitroindole has been focused on its potential as an alternative to the used of mixed bases in PCR or Sanger sequencing primers. However, function of 5-nitroindole is strongly dependent on the location in the primer.

  • Modification Code: 5-N-indole
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y
  • Molecular Weight (mw) 340.23
  • Extinction Coefficient (ec) 16

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Iso-deoxyguanosine (Iso-dG)

so-deoxyguanosine, iso-dG forms a Watson-Crick base pair with 5-methyl iso-dC. Substitution of a iso-dG: 5-Me-iso-dC base pair for a C:G pair increases the Tm of the resulting duplex by ~2degC per base pair substitution. Furthermore, since iso-dG does not pair with dC, 5-Me-iso-dC can function as a stable unnatural base pair that can be used to expand the genetic code.

  • Modification Code: 5-Me-Iso-dG
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y
  • Molecular Weight (mw) 329.21
  • Extinction Coefficient (ec) 4.6

More about Iso-deoxyguanosine (iso-dG) Oligo Modification

K-2'-deoxyribose (dK)

K-2'-deoxyribose, dK is a promising degereate base, this purine derivative can base pair with either C/T mix. It can be use to replace the natural DNA bases with little destabilization, and it has been demonstrated that they can be substituted independently into oligo-nucleotide primers for the polymerase chain reaction.

  • Modification Code: dK
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

More about K-2'-deoxyriobse (dK) Oligo Modification

P-2'-deoxyribose (dP)

P-2'-deoxyribose, dP is a promising degereate base, this pyrimidine derivative can base pair with either G or A. It can be use to replace the natural DNA bases with little destabilization, and it has been demonstrated that they can be substituted independently into oligo-nucleotide primers for the polymerase chain reaction.

  • Modification Code: dP
  • 5 Prime: Y
  • Internal: Y
  • 3 Prime: Y

More about P-2'-deoxyribose Oligo Modification

Mix Bases

Random mix bases, also known as degenerate, wobble, are used in primers to bind to template theat contain variability or a mixture of sequences at primer biding sites. Mixed bases can also be used to create diversity in clone libraries and in site directed mutagenesis.

Bio-Synthesis offers two type of radomization, machine mix and hand mix. Randomization by machine mix has no additional fee. Additional fee apply to hand-mix to any customer-defined percentage composition. Random mixed bases can be introduced at any position in an oligonucleotide.

More about Random Mix Base Oligo Synthesis

Mixed Base
Symbol R Y M K S W H B V D N
Quantity A,G C,T A,C G,T C,G A,T A,C,T C,G,T A,C,G A,G,T A,C,G,T

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